Substituted benzene compounds, process for their preparation, and herbicidal and defoliant compositions containing them

ABSTRACT

Novel herbicidal and defoliant substituted aniline derived compounds represented by general structure (I)  
                 
 
     are described. W, X, Y, Z, and Q are as defined in the disclosure. Also described are the processes for the manufacture of these compounds and agriculturally suitable compositions containing these as active ingredients which are useful as herbicides for general or selective pre-emergent or post-emergent control of undesired plant species and defoliants at very low concentrations of these biologically active compounds

BACKGROUND OF THE INVENTION

[0001] Use of uracils as herbicides ha previously been reported. Forexample, U.S. Pat. Nos. 4,859,229 and 4,746,352 describe 3-phenyl uracilderivatives as herbicides. However the phenyl ring in the describedcompounds carry only four substituents. U.S. Pat. No. 4,927,451describes herbicidal compounds carrying five substituents on the phenylring with a dihydrouracil ring. EP patent 0705829 describes uracilherbicides carrying pentasubstituted phenyl ring with a carbon linkedsubstiutent at position 2 of the phenyl ring. U.S. Pat. Nos. 5,346,881,5,441,925, 5,169,431, 5,476,834, 5,602,077, and WO patents 97/08170,08171, 12886 and 42188 describe uracil herbicides carrying a fusedpentasubstituted phenyl ring where the 2 position of the phenyl ring issubstituted either with a carbon, oxygen or nitrogen. U.S. Pat. No.5,116,404 and JP patent 05025144 describe uracil compounds with a3-phenyl group which may be pentasubstituted but none of these patentsappears to make obvious the compounds of the present invention whichcarry a nitrogen linked substituent at position 2 of the phenyl ringalong with substituents at positions 3, 4,and 6 and there appears to beno indication as to the criticality of the substitution pattern of thephenyl moiety in order to introduce the high herbicidal activity incombination with selectivity towards crops. Similarly use of pyrazole,tetrahydrophthalimide, triazolinone, tetrazolinone, and triazolidinederivatives as herbicides has been described before such as U.S. Pat.Nos. 5,281,571, 4,881,967, 5,084,085, WO patent 85/01939, and Japanesepatent 1-121290 respectively. Pyridazinones, pyridyls, bicyclichydantoins, phthalimides, pyrimidinones, pyrazinones, and pyridinoneshave also been described as herbicides such as WO patents 97/07104,95/02580, 95/23509, EP patent 0786453, WO patents 97/06150, 97/11060,and 97/28127. However, despite the broad coverage of these patents, thegeneral structure of the present invention has not been described.

SUMMARY OF THE INVENTION

[0002] This invention delineates a method for the control of undesiredvegetation in a plantation crop by the application to the locus of thecrop an effective amount of a compound described herein. The herbicidaland defoliant compounds of the present invention are described by thefollowing general formula I or its salts:

[0003] wherein X is hydrogen, halogen, nitro, amino, NHR, N(R)₂, amide,thioamide, cyano, alkylcarbonyl, alkoxycarbonyl, alkylsulfonamide,unsubstituted or substituted alkyl, haloalkyl, alkoxy, haloalkoxy,alkoxycarbonylalkoxy, benzyloxy, aryloxy, or heteroaryloxy;

[0004] Y is hydrogen, halogen, or nitro;

[0005] W is hydrogen, OR, SR, NHR, N(R)₂, CH₂R, CH(R)₂, or C(R)₃,halogen, nitro, or cyano, where multiple R groups represent any possiblecombination of substituents described by R; R is hydrogen, alkyl,alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, alkoxy, cycloalkyloxy,aryloxy, heteroaryloxy, alkylsulfonyl, benzyl, alkylcarbonyl,alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, heteroarylcarbonyl,alkoxycarbonyl, aryloxycarbonyl, or heteroaryloxycarbonyl, where any ofthese groups may be unsubstituted or substituted with any of thefunctional groups represented by one or more of the following: halogen,cyano, nitro, amino, carboxyl, alkyl, haloalkyl, alkylsilyl,alkylcarbonyl, haloalkylcarbonyl, alkoxy, alkoxycarbonyl, haloalkoxy,haloalkoxycarbonyl, alkylsulfonyl, haloalkylsulfonyl, aryl, heteroaryl,or cycloalkyl;

[0006] Q is a heterocycle, examples of which are as follows:

[0007] wherein R₁ is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl,amino, alkoxyalkyl, acetyl, alkoxycarbonylamino, alkylcarbonylamino, oralkoxycarbonyl;

[0008] R₂ is alkyl or haloalkyl;

[0009] R₁ and R₂ could combine to form a five- or six-memberedheterocyclic ring;

[0010] R₃ is hydrogen, halogen, nitro, amino, alkylamino,haloalkylamino, cyano, or amide;

[0011] R₈ and R₉ are independently oxygen, sulfur, or imino group;

[0012] Q6, Q7, and Q10 may optionally be unsaturated containing one ortwo double bonds in the 6-membered ring;

[0013] Z is amino, hydroxyl, thiol, formyl, carboxyl, cyano,alkylcarbonyl, arylcarbonyl, azido, or one of the following:

[0014] wherein R₄ is alkyl, alkenyl, alkynyl, amino, cycloalkyl,heterocycloalkyl, alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl,alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl,arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, alkylthiocarbonyl,cycloalkyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl,aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl,alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl,alkoxycarbonylcarbonyl or arylcarbonylcarbonyl, where any of thesegroups may be unsubstituted or substituted with any of the functionalgroups represented by one or more of the following: halogen, cyano,nitro, amino, dialkylamino, hydroxyl, carboxyl, alkyl, alkenyl, alkynyl,cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy, alkoxycarbonyl,alkylthio, alkylthiocarbonyl, alkoxythiocarbonyl alkylaminocarbonyl,arylaminocarbonyl, alkylsulfonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, heteroaryl, heteroaryloxycarbonyl or methylenedioxy, whereinthe alkyl moiety or aryl moiety may be substituted with halogen, cyano,nitro, alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl,aryl, or heterocycloalkyl; and R₅ is hydrogen or any one of the groupsrepresented by R₄; or R₄ and R₅ could combine to form a 4-8 memberedheterocyclic ring;

[0015] wherein R₆ represents alkyl, haloalkyl, dialkylamino,unsubstituted or substituted aryl and heteroaryl; and R₇ representshydrogen, halogen or any of the groups represented by R₆;

[0016] —OR₄,

[0017] —SR₄,

[0018] —CH₂R₁₀,

[0019] —CH(R₁₀)₂,

[0020] —C(R₁₀)₃, or

[0021] —CH═CHR₁₀

[0022] wherein R₁₀ is carboxyl, alkyl, alkenyl, alkynyl, amino,cycloalkyl, heterocycloalkyl, alkylsulfonyl, arylsulfonyl, benzyl, aryl,heteroaryl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxyc arbonyl,alkylthiocarbonyl, cycloalkyloxy carbonyl, aryloxy carbonyl,arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl,aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl,heteroarylaminocarbonyl, alkoxycarbonylcarbonyl or arylcarbonylcarbonyl,where any of these groups may be unsubstituted or substituted with anyof the functional groups represented by one or more of the following:halogen, cyano, nitro, amino, dialkylamino, hydroxyl, carboxyl, alkyl,alkenyl, alkynyl, cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy,alkoxycarbonyl, alkylthio, alkylthiocarbonyl, alkoxythiocarbonylalkylaminocarbonyl, arylaminocarbonyl, alkylsulfonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy,aryloxycarbonyl, arylthio, heteroaryl, heteroaryloxycarbonyl ormethylenedioxy, wherein the alkyl moiety or aryl moiety may besubstituted with halogen, cyano, nitro, alkyl, alkoxy, haloalkyl,haloalkoxy, alkoxycarbonyl, cycloalkyl, aryl, or heterocycloalkyl;

[0023] provided that (1) Z is not alkyl, alkoxy, haloalkyl, haloalkoxy,alkylthio, haloalkylthio, alkenyl, haloalkenyl, amino, monoalkylamino,dialkylamino, alkoxyalkoxy or cyano, when Q is Q1 and R₂ is haloalkyl,

[0024] (2) Z is not amino when Q is Q3, and

[0025] (3) Z is not hydroxyl, alkoxy, alkenyloxy, alkynyloxy,haloalkoxy, haloalkenyloxy, or —NR₄R₅, wherein R₄ is alkyl, alkenyl,alkynyl, cycloalkyl, haloalkyl, haloalkenyl, alkylsulfonyl,alkylcarbonyl, alkoxycarbonyl, or cycloalkylalkyl, and R₅ is alkyl,alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, alkylcarbonyl,alkoxycarbonyl, or cycloalkylalkyl, when Q is Q14 or Q15.

DETAILED DESCRIPTION OF THE INVENTION

[0026] In the above definitions, the term alkyl used either alone or incompound words such as haloalkyl indicates either straight chain orbranched alkyls containing 1-8 carbon atoms. Alkenyl and alkynyl includestraight chain or branched alkenes and alkynes respectively containing2-8 carbon atoms. The term halogen either alone or in the compound wordssuch as haloalkyl indicates fluorine, chlorine, bromine, or iodine.Further a haloalkyl is represented by an alkyl partially or fullysubstituted with halogen atoms which may be same or different. Acycloalkyl group implies a saturated or unsaturated carbocyclecontaining 3-8 carbon atoms. A heterocycloalkyl group is a cycloalkylgroup carrying 1-4 heteroatoms which are representd by oxygen, nitrogen,or sulfur atoms. An aryl group signifies an aromatic carbocyclecontaining 4-10 carbon atoms, and may be phenyl or naphthyl. Aheteroaryl group is an aromatic ring containing 1-4 heteroatoms whichare represented by oxygen, nitrogen, or sulfur atoms, and may forexample be furanyl, pyridyl, thienyl, pyrimidinyl, benzofuranyl,quinolyl, benzothienyl or quinoxalyl.

[0027] The compound of the formula I may form a salt with an acidicsubstance or a basic substance. The salt with an acidic substance may bean inorganic acid salt such as a hydrochloride, a hydrobromide, aphosphate, a sulfate or a nitrate. The salt with a basic substance maybe a salt of an inorganic or organic base such as a sodium salt, apotassium salt, a calcium salt, a quaternary ammonium salt such asammonium salt or a dimethylamine salt.

[0028] The compound of the formula I may exist as geometrical or opticalisomers and the present invention includes all of these isomeric forms.

[0029] Preferred compounds for the reasons of ease of synthesis orgreater herbicidal efficacy are represented by the formula I wherein

[0030] (1) Z is —NR₄R, or —CH₂R₁₀,

[0031] (2) X is halogen or cyano; Y is halogen; W is —OR; and R isalkyl, alkenyl, or alkynyl, where any of these groups may beunsubstituted or substituted with any of the functional groupsrepresented by one or more of the following: halogen, cyano, nitro,amino, or carboxyl, or

[0032] (3) Q is Q1 or Q6; R₁ is alkyl, amino or haloalkyl; R₂ ishaloalkyl; R₃ is hydrogen; and R₈ and R₉ are independently oxygen,sulfur, or imino group,

[0033] Still more preferred compounds for the reasons of greaterherbicidal efficacy are represented by formula I wherein

[0034] X is halogen; Y is fluorine; W is OR; R is alkyl, alkenyl, oralkynyl, where any of these groups may be unsubstituted or substitutedwith halogen or cyano; Q is Q1 or Q6; R₁ is alkyl, amino, or haloalkyl;R₂ is haloalkyl; R₃ is hydrogen; and R₈ and R₉ are independently oxygen,sulfur, or imino group; Z is —NR₄R₅; R₄ is alkylcarbonyl,alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl,heteroarylcarbonyl, alkoxycarbonyl, alkylthiocarbonyl,cycloalkyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl,aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl,alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl,alkoxycarbonylcarbonyl, arylcarbonylcarbonyl, where any of these groupsmay be unsubstituted or substituted with any of the functional groupsrepresented by one or more of the following: halogen, cyano, nitro,amino, dialkylamino, hydroxyl, carboxyl, alkyl, alkenyl, alkynyl,cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy, alkoxycarbonyl,alkylthio, alkylthiocarbonyl, alkoxythiocarbonyl alkylaminocarbonyl,arylaminocarbonyl, alkylsulfonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, heteroaryl, heteroaryloxycarbonyl, or methylenedioxy, whereinthe alkyl moiety or aryl moiety may be substituted with halogen, cyano,nitro, alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl,aryl, or heterocycloalkyl; and R₅ is hydrogen; or Z is —CH₂R₁₀; R₁₀ iscarboxyl, alkyl, alkenyl, or alkynyl, where any of these groups may beunsubstituted or substituted with any of the functional groupsrepresented by one or more of the following: halogen, cyano, nitro,amino, dialkylamino, hydroxyl, carboxyl, alkyl, alkenyl, alkynyl,cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy, alkoxycarbonyl,alkylthio, alkylthiocarbonyl, alkoxythiocarbonyl alkylaminocarbonyl,arylaminocarbonyl, alkylsulfonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, heteroaryl, heteroaryloxycarbonyl, or methylenedioxy, whereinthe alkyl moiety or aryl moiety may be substituted with halogen, cyano,nitro, alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl,aryl, or heterocycloalkyl.

[0035] Certain intermediates of the present invention are novel. Theseare3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione,3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-amino-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneand represented by the following formulae (III-V):

[0036] wherein X, Y, W and Q are the same as defined above; and M isnitro.

[0037] wherein X′ and Y′ are halogens; and R is the same as definedabove.

[0038] The compounds described by the formula I can be prepared by theprocedures as described herein. In general, the compounds described inthis invention can be prepared by one of the two routes depending onwhether the heterocyclic ring (e.g. uracil ring) is formed prior to orafter the nitration at the 2 position of the phenyl ring in the finalproduct.

[0039] As depicted in Scheme 1, the starting materials for thesepreparations are the compounds represented by the formula VIc. Thesecompounds can be prepared starting from the nitro compound VIa via theamine VIb by the procedures described in literature, for example U.S.Pat. No. 4,859,229 (1989). Nitration of Vic is typically carried out byits slow addition to a mixture of sulfuric acid and nitric acid in aratio of 9:1. Typically 3-4 ml of the nitration mixture is used for 2-3mmol of VI and the addition is carried out between 0 to −30° C. followedby stirring at ambient temperature for 0.5-2 hr. Product (VII) isseparated by addition of the solution to ice water and filtration of theprecipitate. The product can also be extracted from aqueous layer intoorganic solvents such as ether or ethyl acetate and purified bycrystallization or column chromatography. Alkylation of VII to VIII canbe accomplished by treatment of VII with alkyl halide, haloalkyl halide,especially the respective chloride, bromide, or sulfate in the presenceof a base such as potassium carbonate or sodium hydride in an inertsolvent such as acetone, dimethylformamide, dimethylsulfoxide,tetrahydrofuran, methyl ethyl ketone, or acetonitrile at a temperaturerange of 0 to 130° C. VIII can be reduced to the amine (IX) undertypical reduction conditions such as treatment with iron in acetic acidor ethanolic hydrochloric acid; or by hydrogenation using palladium oncarbon or platinum oxide as catalyst. The product IX is purified bytypical purification procedures of recrystallization or columnchromatography.

[0040] The amine (IX) can be derivatized to yield a variety of productsgenerally represented by the formula X. For example amides can beprepared by treatment of IX with alkyl or aryl acid halides, typicallychlorides, or anhydrides in the presence of base in an inert solvent.Typically organic bases such as triethylamine, diisopropylethylamine, orpyridine can be used in inert solvents such as tetrahydrofuran,acetonitrile, or dioxane at a temperature range of ambient to refluxtemperature for 2-24 hr. Pyridine can be used alone as solvent and base.Acylation catalysts such as dimethylaminopyridine (DMAP) can be added tofacilitate the reaction. Typical work-up procedure includes removal ofsolvent followed by partitioning of the product between aqueous andorganic solvents such as ether, ethyl, acetate or methylene chloride.Depending upon the reactivity of the acid halide, the product typicallyconsists of a monoamide, diamide, or a mixture of the two. These can bepurified/resolved typically by column chromatography. Mono or dialkyl(amino) derivatives of IX can be prepared by its treatment with alkyl orhaloalkyl halides in the presence of base such as potassium or sodiumcarbonate, or sodium hydride in an inert solvent such as tertahydrofaranor dimethylformamide at a temperature of ambient to 120° C. for 2-24 hr.Mono or dicarbamoyl derivatives of IX can be prepared by its treatmentwith alkylhaloformates such as methyl or ethylchloroformate in thepresence of base such as potassium or sodium carbonate in an inertsolvent such as tertahydrofaran or dimethylformamide at a temperature ofambient to 120° C. for 2-24 hr. Mono or diurea derivatives of IX can beprepared by its treatment with an alkyl or aryl isocyanate, for examplemethyl or ethyl isocayante, in the presence of a base such astriethylamine in an inert solvent such as toluene or tetrahydrofuran.Alternatively, IX is first converted into its isocyanate derivative bytreatment with phosgene or triphosgene in toluene or tetrahydrofuran atreflux temperature for 2-6 hr. This isocyanate can, in turn, be treatedwith an alkyl or aryl amine such as methyl or ethyl amine in thepresence of a base such as triethylamine in an inert solvent such astoluene or tetrahydrofuran at a temperature range of ambient to 130° C.for 2-12 hr to furnish the corresponding urea. IX can be treated with analkyl dihalide such as 1,4-diiodobutane in an inert solvent such astoluene or acetonitrile at reflux temperature in the presence of a basesuch as potassium or sodium carbonate to furnish the correspondingcyclized product such as a pyrrolidine derivative. IX can be treatedwith an aromatic or aliphatic aldehyde or ketone or its diethyl ordimethyl acetal derivative in an inert solvent such as toluene ormethylene chloride to furnish the corresponding imino derivative.Alternatively, a monoacetyl derivative of IX can be treated with adehydrochlorinating agent such as phosphorus pentachloride to furnishthe corresponding iminochloride.

[0041] The starting uracil derivative represented by formula XI inScheme 2 can be prepared according to the procedure as described before.The compound XI is nitrated with concentrated nitric acid at 0° C. toambient temperature for 15˜30 minutes. Product (XII) is obtained byaddition of the product mixture to ice-water followed by filtration.

[0042] The starting uracil derivative represented by formula XIII inScheme 3 can be prepared according to the procedure as previouslydescribed. Compound XIII can be nitrated with nitric acid at 0° C. for15˜30 minutes. Product (XIV) is obtained by addition of ice followed byfiltration.

[0043] The desired starting tetrazole derivatives represented by formulaXV in Scheme 4 can be prepared according to the literature procedure ofWO 85/01939. These compounds can be nitrated with nitric acid at ambienttemperature or at 0° C. for 15˜30 minutes. Product (XVI) is isolated byaddition of ice followed by extraction into an organic solvent such asether or ethyl acetate and purified. XVII can be prepared by thereduction of XVI typically by catalytic hydrogenation in presence ofcatalysts such as palladium on carbon or by treatment with iron inacetic acid or in ethanolic hydrochloric acid. XVIII can be prepared byreacting XVII with a halide in presence of a base at 50 to 120° C. for1˜5 hours. Further modification of XVIII to XIX is carried out accordingto the general procedures described for the preparation of X from IX(Scheme I).

[0044] The starting triazolinone derivative represented by formula XX inScheme 5 can be prepared according to the literature procedure of U.S.Pat. No. 4,980,480 (1990). The compound XX is nitrated with concentratednitric acid at −15 to 0° C. for 0.5-2 hr. Product (XXI) is obtained byaddition of the product mixture to ice-water followed by filtration.

[0045] The desired starting pyrazole derivatives represented by formulaXXII in Scheme 6 can be prepared according to the literature procedureof U.S. Pat. No. 5,281,571 (1994). These compounds can be nitrated insulfuric acid-nitric acid mixture (9:1) with a ratio of 3-4 ml of thenitrating solution to 3-4 mmol of XXII. The addition is carried outbetween -15 to −30° C. followed by stirring at ambient temperature for1-2 hr. Product (XXIII) is isolated by addition of water followed byextraction into an organic solvent such as ether or ethyl acetate andpurified. XXIV can be prepared by the reduction of XXIII typically bycatalytic hydrogenation in presence of catalysts such as palladium oncarbon or by treatment with iron in acetic acid or in ethanolichydrochloric acid. Further modification of XXIV to XXV is carried outaccording to the general procedures described for the preparation of Xfrom IX (Scheme I).

[0046] The desired starting tetrahydrophthalimide derivative representedby formula XXVI in Scheme 7 can be prepared according to the literatureprocedure of U.S. Pat. No. 4,484,941 (1984). The compound can benitrated with nitric acid at 0° C. to ambient temperature for half hour.The product (XXVII) is isolated by addition of ice followed byextraction into an organic solvent such as ether, ethyl acetate, ormethylene chloride and purified. XXVIII can be prepared by the reductionof XXVII typically by catalytic hydrogenation in presence of catalystssuch as palladium on carbon or by treatment with iron in acetic acid orin ethanolic hydrochloric acid. XXIX can be prepared by reacting XXVIIIwith (substituted)alkyl halide in the presence of a base such aspotassium carbonate. Further modification of XXIX to XXX is carried outaccording to the general procedures described for the preparation of Xfrom IX (Scheme I).

[0047] Scheme 8 describes the preparation of intermediates representedby the formulae XXXIII and IV. The starting materials (amino phenols andalkyl derivatives represented by the formula VIb) are prepared accordingto the procedure as described in literature such as U.S. Pat. No.4,670,046 (1987) which upon treatment with phthalic anhydride in aceticacid can afford phthalimide derivative (XXXI). Nitration of XXXI can becarried out by its addition to a mixture of sulfuric acid and nitricacid (9:1) at −15 to −30° C. followed by addition of water andextraction of the product (XXXII) in organic solvents such as ethylacetate or ether. XXXII can be reduced to the corresponding amine(XXXIII) by conventional methods such as treatment with iron in aceticacid or ethanolic hydrochloric acid or by catalytic hydrogenation in thepresence of palladium on carbon. Amino group of XXXIII can bederivatized as described before in Scheme 1 to furnish XXXIV which inturn can be deprotected to furnish XXXV. Removal of the protectingphthalimido group can be accomplished by several methods such astreatment with hydrazine in a polar solvent such as dimethylsulfoxide orby treatment with on organic amine such as methyl amine in ethanol. XXVcan then be derivatized to the desired compound (X) according to theknown procedures as described before in Schemel. Alternatively, XXXIIcan first be subjected to deprotection to afford the amine IV which canbe modified to introduce the heterocyclic ring such as the uracil ring(U in XXXVI) according to the known procedures. Nitro group in XXXVI canthen be reduced to afford the amine which can then be derivatized asdescribed previously to afford X.

[0048] Scheme 9 delineates a process for the preparation of theintermediates represented by the formula V. Starting materialsrepresented by the formula XXXIX are prepared by the nitration of XXXVIIwhich gives XXXVIII which can be reduced to XXXIX according to theliterature procedure of Japanese patent 01186849 (1989). The amino groupin XXXIX is protected by forming amide or carbamate XL and the latter isnitrated to give XLI. Deprotection of XLI leads to the ortho-nitroaniline V. V can be converted into the desired compounds represented byXLV according to the procedures as shown in the scheme.

[0049] Scheme 10 describes the preparation of intermediate representedby the formulae XLVIII. The starting material (XLVI) can be preparedaccording to the method described in patents, such as U.S. Pat. No.5,154,755 (1992). XLVI reacts with ethyl chloroformate at basiccondition to give the carbamate XLVII. The latter is nitrated with amixture of nitric acid and sulfuric acid to give the intermediate XLVIIIwhich can be N-alkylated with an alkylhalide in the presence of base tofurnish XLIX.

[0050] Scheme 11 describes an alternative procedure for the preparationof compounds represented by the formula LVII with varying R groups.Reduction of L to LI is carried out using conventional procedures suchas catalytic reduction or iron-acetic acid mixture. The aniline LI isreacted with phenyl chloroformate to afford a carbamte represnted by theformula LII which is nitrated with an inorganic salt such as ammonium orpotassium nitrate in an acid anhydride such as acetic anhydrideaccording to published perocedure such as described in WO 97/42188.Resultant nitro derivative LIII is cyclized to furnish the uracilderivative LIV upon reaction with an appropriately substituted aminocrotonate in the presence of an inorganic or organic base exemplified by1,8-diazabicylo[5.4.0]undec-7-ene (DBU). LIV is N-derivatized to affordLV followed by reduction to aniline LVI according to conventionalprocedures as described before. LVII is then derivatized to afford thefinal compounds represented by the formula LVII according to theprocedures as described before.

[0051] Scheme 12 desribes a process for the preparation of compoundsrepresented by the formula LXII which are trisubstituted phenylderivatives. Ortho-nitroaniline derivatives represented by the formulaLVIII are the starting materials which are converted to a ortho-nitrouracil derivatives (LX) according to previously described procedures,e.g. via the NH uracil derivative (LIX). Nitro groups is then convertedto an amino group (LXI) via conventional reduction procedures such ascataytic or iron-acetic acid reduction followed by derivatization tofurnish LXII.

[0052] Scheme 13 describes a procedure for the preparation oftrisubstituted phenyl derivatives represented by the formula LXVI.Direct nitration of LXIII, where X and Q (a heterocylce) are aspreviously defined, using nitration reagents such as nitric acid or amixture of sulfuric acid-nitric acid leads to ortho-nitro compoundsrepresented by the formula LXIV which are reduced to the correspondinganiline derivatives (LXV) by reduction procedures such as catatlyticreduction or iron-acetic acid. Aniline (LXV) is then derivatized tofurnish LXVI.

[0053] Scheme 14 delineates a procedure for the preparation oftetrasubstituted phenyl derivatives represented by the formula LXXIV.The process is akin to one described in scheme 11 for the prepration ofpentasubstituted phenyl derivatives (LVII). The nitro intermediates(LXVII) are reduced to the anilines (LXVIII) via conventional proceduresfollowed by derivatization to the phenyl carbamate (LXIX) by reactionwith a phenylhaloformate. Nitration to LXX (inorganic nitrate-acidanhydirde) is followed by the uracil ring formation (appropriatelysubstituted crotonate-DBU) (LXXI) and N-derivatization to furnish LXXII.Reduciton to the aniline (LXXIII) is carried out by procedures such ascatalytic reduction or iron-acetic acid followed by derivatization tofurnish LXXIV.

[0054] Scheme 15 describes vaious procedures for the derivatization ofthe amino group in LXXV via diazonium salts represented by LXXVI. Thediazonium salts are prepared by treatment of the aniline with aninorganic nitrite solution such as sodium or potassium nitrite in anacid such as sulfuric or hydrochloric acid or by treatment of theaniline with an organic nitrite such as t-butyl nitrite in an organicsolvent such as acetonitrile. Reaction is carried out between 10-−15° C.which results in a stable solution of the diazonium salt which isreduced to the corresponding hydrazine derivative represented by theformula LXXVII by reducing agents exemplified by stannic chloride.Hydrazine derivatives are then derivatized to a variety of compoundsrepresented by the formula (LXXXVI) via Conventional reacions such asacylation, alkylation, Schiff base formation, etc. The diazonium groupin LXXVI is replaced by a hydroxyl to furnish the corresponding phenol(LXXVIII) by its treatment with an aqueous solution of cuprous oxide inpresence of cupric nitrate or cupric sulfate at ambient temperature.LXXVIII is then derivatized to furnish LXXXVI via conventional reactionssuch as acylation, alkylation, etc. Treatment of the diazonium salts(LXXVI) with disulfides (RSSR) leads to the formation of correspondingthioethers represented by the formula LXXIX which can be furthermodified according to conventional procedures leading to sulfur analogsrepresented by the formula LXXXVI. LXXVI can be treated with inorganiccyanides leading to the formation of cyano derivatives (LXXXI) which canbe oxidized via conventional routes to furnish carboxylic acids (LXXXV)which can then be derivatized leading to LXXXVI. The diazonium group canalso be replaced with an azido group furnishing LXXX. LXXVI can betreated with inorganic iodides to afford the iodo compounds (LXXXII)which can be converted to the corresponding aldehydes (LXXXIII) (whichare also directly obtainable from LXXVI via conventional procedures).LXXXIII can be reduced to furnish corresponding benzyl alcohols (LXXXIV)which can be derivatized to LXXXVI.

[0055] Scheme 16 describes an alternatived procedure for the formationof amides (XC). Reaction of the ortho-amino phenol LXXXVII with analiphatic or aromatic acyl halide in an organic solvent such as1,4-dioxane or tetrahydrofuran in the absence or presence of aninorganic or organic base such as potassium carbonate, sodium carbonate,or triethylamine, regioselectively leads to the formation ofcorresponding amide represented by the formula LXXXIX. LXXXIX can alsobe produced by the hydrolysis of a corresponding alkyl ether such asmethyl ether (LXXXVIII) by treatment with strong Lewis acids such asboron tribromide or boron tribromide-dimethyl sulfide complex. Phenolgroup in LXXXIX is then derivatized by treatment with a halide in thepresence of base such as sodium carbonate or potassium carbonate in anorganic solvent such as as acetone, methyt-ethyl ketone,dimethylsulfoxide, or tetrahydrofuran at ambient to reflux temperatures.

[0056] Scheme 17 describes a procedure for the preparation ofpyridazinone derivatives represented by the formula XCVII and XCVIII.Desired starting pyridazinone derivatives represented by formula XCI andXCIV can be prepared according to the literature procedure of WO97/07104. These compounds can be nitrated with nitric acid or a mixtureof nitric acid and sulfuric acid at ambient temperature or at 0° C. for15˜30 minutes. The products XCII and XCV are isolated by addition of icefollowed by filtration. XCIII and XCVI can be prepared by the reductionwith iron in acetic acid or in ethanolic hydrochloric acid. Methylationof XCIII can be carried out by reacting XCIII with methyl iodide inpresence of a base at 50 to 120° C. for 1˜5 hours. Further modificationof XCVI to XCVIII is carried out by treatment of the aniline with anorganic nitrite (such as t-butyl nitrite) in an organic solvent (such asacetonitrile) and alkyl acrylate in the presence of copper(II) chloride.Modification of XCVI to XCVII is carried out by treatment of the anilinewith an alkyl or aryl acid halide at 50 to 120° C. for 1˜5 hours.

EXAMPLE 1 Preparation of3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. I1-1)

[0057] 3-(4-Chloro-6-fluoro-3-methoxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (10.0 g, 29.5 mmol) was slowly added to a stirredmixture of con. sulfuric acid (36 ml) and con. nitric acid (4 ml) withstirring at −15° C. The solution was then slowly warmed to roomtemperature and allowed to stir for 2 hr. Addition of the solution toice-water resulted in a light yellow precipitate which was separated byfiltration to afford the title compound (9.1 g). NMR data for thecompound are listed in Table XVIII.

EXAMPLE 2 Preparation of3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-5)

[0058]3-(4-Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (9 g, 23.5 mmol) was dissolved in dimethylformamide(90 ml) and to this were added potassium carbonate (3.9 g, 28.2 mmol)and dimethylsulfate (10.2 g, 47 mmol) with stirring. The solution wasstirred at ambient temperature for 12 hr and water was added. Productwas extracted in ethyl acetate and the organic layer was washed withwater and dried over anhydrous sodium sulfate. Removal of the solventafforded a crude product which was purified by column chromatography onsilica gel. Elution of the column with methylene chloride afforded thetitle compound (7.8 g).

EXAMPLE 3 Preparation of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-4)

[0059]3-(4-Chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (7.5 g, 18.9 mmol) was dissolved in acetic acid (75ml) and 4.2 g (75.6 mmol) of iron powder was added. The solution wasstirred at ambient temperature under nitrogen atmosphere for 6 hr andwater was added. Extraction was carried out with ethyl acetate. Organiclayer was washed with water, brine, and dried with anhydrous sodiumsulfate followed by evaporation to afford the title compound (6.8 g).

EXAMPLE 4 Preparation of3-[4-chloro-2-(2,4-difluorobenzoyl)amino-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-42)

[0060]3-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (2.0 g, 5.4 mmol) and triethylamine (0.66 g, 6.5mmol) were dissolved in anhydrous tetrahydrofuran (30 ml) and stirredunder ice cooling. To this solution was slowly added 2,4-difluorobenzoylchloride (0.96 g, 5.4 mmol) and solution refluxed for 2 hr. Anotherbatch of 2,4-difluorobenzoyl chloride (0.19 g, 1.1 mmol) was added andsolution refluxed for 2 hr. Solvent was removed in vacuo and the productpurified by column chromatography on silica gel using hexane-ethylacetate (3:1) as the eluent to afford the title compound (2.2 g).

EXAMPLE 5 Preparation of3-(4-chloro-2-diacetylamino-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-2)

[0061] A mixture of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.5 g, 1.4 mmol), triethylamine (0.53 g, 5.6 mmol),acetic anhydride (0.57 g, 5.6 mmol), and anhydrous toluene (10 ml) wasrefluxed for 12 hr. Solvent was removed in vacuo and the productpurified by chromatography on silica gel. Column was eluted withhexane-ethyl acetate (7:3) to furnish the title compound (0.34 g).

EXAMPLE 6 Preparation of3-(4-chloro-2-dimehtylamino-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-11)

[0062] To a solution of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.6 g, 1.6 mmol) in toluene (10 ml) was addedpotassium carbonate (0.27 g, 1.92 mmol) followed by dimethylsulfate(0.69 g, 3.2 mmol). The solution was refluxed for 2 hr and solvent wasremoved in vacuo. Residue was chromatographed on silica gel and producteluted with methylene chloride to afford the title compound (0.12 g).

EXAMPLE 7 Preparation of3-(4-chloro-6-fluoro-3-methoxy-2-methoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 4-1)

[0063] A solution of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.25 g) and triethylamine (1 ml) in ethyl acetate(20 ml) was added to a solution of triphosgene (1.0 g) in ethyl acetate(15 ml) stirred under nitrogen. The mixture was heated at reflux for 2hr, cooled, filtered and the filtrate evaporated under reduced pressureto give a buff colored solid (1.4 g). ¹H NMR (CDCl₃, 300 MHz) 3.58 (3H,s), 4.00 (3H, s), 6.38 (1H, s), 7.12 (1H, d, J=8.8 Hz) ppm.

[0064] The above isocyanate (0.5 g) dissolved in N,N-dimethylformamide(10 ml) was treated with dry methanol (2 ml) and stirred at roomtemperature for two days. Water and ethyl acetate were added and thesolution separated. The organic phase was dried over sodium sulfate,evaporated, and chromatographed on silica gel eluting with ethylacetate-hexane (1:3) to give the title compound as a white solid (0.17g).

EXAMPLE 8 Preparation of3-[2-bis(methylaminocarbonyl)amino-4-chloro-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 3-1)

[0065] To a solution of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.5 g, 1.4 mmol) and triethylamine (0.17 g, 1.7mmol) in anhydrous toluene (10 ml) was added methyl isocyanate (0.1 g,1.7 mmol) with stirring. The solution was refluxed for 2 hr and solventremoved. Residue was chromatographed on silica gel in methylenechloride-methanol (99:1) to furnish the title compound (0.56 g).

EXAMPLE 9 Preparation of3-[4-chloro-2-(dimethylaminomethynyl)imino-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-31)

[0066] A mixture of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.5 g, 1.4 mmol) and dimethylformamidedimethylacetal (0.8 g, 7 mmol) was refluxed for 4 hr under a blanket ofnitrogen. Excess reagent was removed in vacuo and product extracted withether. Solvent was removed to afford a residue which was chromatographedon silica gel. Elution of the column with hexane-ethyl acetate (6:4)afforded the title compound (0.22 g).

EXAMPLE 10 Preparation of3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-16)

[0067]3-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.1 g, 2.7 mmol) was dissolved in 50 ml ofanhydrous 1,2-dichloroethane and 3.4 g (10.8 mmol) ofborontribromide-dimethylsulfide complex was added to the solution. Thesolution was refluxed for 16 hr and methylene chloride (100 ml) wasadded. Washing with water followed by drying (anhydrous sodium sulfate)and removal of the solvent afforded a residue which was triturated withether to afford the title compound (0.6 g).

EXAMPLE 11 Preparation of3-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-2)

[0068]3-(4-chloro-2-fluoro-5-hydroxyphenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione(2.5 g) was added to an ice cooled con. nitric acid (50 ml). Afterstirring for 1 hr, the reaction mixture was poured into ice-cold water.The yellow crystals were collected by filtration to afford the titlecompound (0.9 g). The filtrate was extracted by ethyl acetate (200 ml)and washed with brine. The organic phase was dried over anhydrous sodiumsulfate. After removal of the solvent, 0.6 g of title compound wasobtained as yellow crystal.

EXAMPLE 12 Preparation of3-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-17)

[0069]3-(4-Chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.06 g) was added to ice-cold con. nitric acid (10ml). After stirring for 30 min, crushed ice was added. The yellowcrystals were collected by filtration to afford the title compound (1.2g).

EXAMPLE 13 Preparation of1-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-4-(3-fluoropropyl)-1,4-dihydro-5-oxo-5H-tetrazole(Compound no. 5-4)

[0070]1-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-(3-fluoropropyl)-tetrazolinone(2.91 g) was gradually added into an ice-cooled nitric acid (20 ml) andstirred for 30 minutes. Crushed ice was added followed by extractionwith ethyl acetate. The ethyl acetate extract was washed with water,dried over sodium sulfate, concentrated, and filtered through a silicagel SPE column (2 g) to give the title compound as a yellow solid (3.4g).

EXAMPLE 14 Preparation of1-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-4-(3-fluoroproyl)-1,4-dihydro-5-oxo-5H-tetrazole(Compound no. 5-5)

[0071] Iron powder (2.3 g) was added to a solution of1-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-4-(3-fluoropropyl)-1,4-dihydro-5-oxo-5H-tetrazole(3.4 g) in acetic acid (50 ml) and stirred at room temperature overnight. The reaction mixture was filtered through a celite bed. Thefiltrate was concentrated under reduced pressure and purified by asilica gel column, eluted with hexane-ethyl acetate (2:1) to give yellowcrystals (2.75 g).

EXAMPLE 15 Preparation of1-(2-amino-4-chloro-6-fluoro-3-propargyloxyphenyl)-4-(3-fluoroproyl)-1,4-dihydro-5-oxo-5H-tetrazole(Compound no. 5-17)

[0072] The mixture of1-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-4-(3-fluoropropyl)-tetrazolinone(0.28 g), propargyl bromide (0.13 g), and potassium carbonate (0.14 g)in acetonitrile (5 ml) was heated under reflux for 0.5 hour. The solventand excess reagent were removed under reduced pressure. The residue waspurified by a silica gel column, eluted with ethyl acetate to give thedesired product (0.33 g).

EXAMPLE 16 Preparation of1-(2-amino-4-chloro-6-fluoro-3-isopropyloxyphenyl)-4-(3-fluoropropyl)-1,4-dihydro-5-oxo-5H-tetrazole(Compound no. 5-18)

[0073] The mixture of1-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-4-(3-fluoropropyl)-1,4-dihydro-5-oxo-5H-tetrazole(0.30 g), isopropyl iodide (1.2 ml), and potassium carbonate (0.14 g) inacetonitrile (5 ml) was heated under reflux for 2 hours. The reactionmixture was evaporated and purified by a silica gel column, eluted withhexane-ethyl acetate (2:1) to give the desired product (0.29 g).

EXAMPLE 17 Preparation of1-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-4-difluoromethyl-3-methyl-1,2,4-triazolinone(Compound no. 6-1)

[0074]1-(4-Chloro-2-fluoro-5-hydroxyphenyl)-4-difluoromethyl-3-methyl-1,2,4-triazolinone(0.21 g) was added to con. nitric acid (1.5 ml) at ambient temperature.The solution was vigorously stirred at ambient temperature for 15 min.Reaction mixture was poured into ice-cold water and yellow precipitatewas collected by filtration to afford the title compound (0.17 g) as a1:1 mixture with oxidative compound.

EXAMPLE 18 Preparation of1-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-4-difluoromethyl-3-methyl-1,2,4-triazolinone(Compound no. 6-2)

[0075] To a stirred solution of1-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenol)-4-difluoromethyl-3-methyl-1,2,4-triazolinone(0.15 g) in a mixed solvent of con. hydrochloric acid (5 ml) andmethanol (5 ml) was added 0.3 g of iron powder at ambient temperature.The resulting mixture was refluxed for 1 hr and the solution wasconcentrated under reduced pressure. The residue was extracted withethyl acetate (200 ml) and the organic phase was washed with brine anddried over anhydrous sodium sulfate. Solvent was removed under reducedpressure to give title compound as a brown oil.

EXAMPLE 19 Preparation of4-chloro-3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole(Compound no. 7-1)

[0076]4-Chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole(1.2 g, 3.5 mmol) was slurried with 4 ml of con. sulfuric acid and wasslowly added to a stirred 4 ml mixture of con. sulfuric acid-con. nitricacid (9:1) at −15° C. Solution was allowed to stir at ambienttemperature for 2 hr and then added to ice water. Extraction with ethylacetate and removal of the solvent afforded a crude product which waschromatographed on silica gel. Elution of the column withhexane-methylene chloride (4:6) furnished the title compound (0.72 g).

EXAMPLE 20 Preparation of4-chloro-3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole(Compound no. 7-2)

[0077]4-Chloro-3-(4-chloro-6-fluoro-3-methoxy-2-nitrophenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole(0.48 g, 1.24 mmol) was dissolved in toluene (8 ml) and 0.05 g of 10%palladium on carbon was added. The solution was vigorously stirred underhydrogen atmosphere for 4 hr at ambient temperature and the catalyst wasremoved by filtration. Removal of the solvent afforded a residue whichwas chromatographed on silica gel. Elution of the column withhexane-methylene chloride (3:7) furnished the title compound (0.38 g).

EXAMPLE 21 Preparation of6-chloro-4-fluoro-2-nitro-3-(tetrahydrophthalimido)phenol (Compound no.8-1)

[0078] 2-Chloro-4-fluoro-5-(tetrahydrophthalimido)phenol (5.0 g) wasadded into nitric acid (50 ml) at 0° C., warmed up to room temperaturein 30 minutes. Crushed ice was added and the solution extracted withmethylene chloride. The organic phase was washed with water, dried overanhydrous sodium sulfate, and purified by a silica gel column, elutedwith methylene chloride-ethyl acetate (19:1) to give 3.67 g of thedesired product.

EXAMPLE 22 Preparation of2-amino-6-chloro-4-fluoro-3-(tetrahydrophthalimido)phenol (Compound no.8-2)

[0079] Iron powder (2.48 g) was added into a solution of6-chloro-4-fluoro-2-nitro-3-(tetrahydrophthalimido)phenol (3.67 g) inacetic acid (60 ml) and stirred at room temperature for two hours. Thereaction mixture was diluted with ethyl acetate, washed with water,dried over anhydrous sodium sulfate, evaporated to give 3.6 g of thetitle compound.

EXAMPLE 23 Preparation ofN-(2-amino-4-chloro-6-fluoro-3-propargyloxyphenyl)tetrahydrophthalimide(Compound no. 8-3)

[0080] A mixture of2-amino-6-chloro-4-fluoro-3-(tetrahydrophthalimido)phenol (0.31 g),propargyl bromide (0.2 ml), potassium carbonate (0.14 g), andacetonitrile (5 ml) was heated under reflux for 0.5 hr. The solvent andexcess reagent were removed under reduced pressure. The residue waspurified by a silica gel column, eluted with ethyl acetate to give thetitle product (0.2 g).

EXAMPLE 24 Preparation ofN-(2-amino-4-chloro-6-fluoro-3-isopropyloxyphenyl)tetrahydrophthalimide(Compound no. 8-4)

[0081] A mixture of2-amino-6-chloro-4-fluoro-3-(tetrahydrophthalimido)phenol (0.31 g),isopropyl iodide (1.2 ml), potassium carbonate (0.14 g), andacetonitrile (5 ml) was heated under reflux for 2 hr. The solvent andexcess reagent were removed under reduced pressure. The residue waspurified by a silica gel column, eluted with ethyl acetate to give thetitle product (0.21 g).

EXAMPLE 25 Preparation ofN-(2-amino-4-chloro-3-cyclopentyloxy-6-fluorophenyl)tetrahydrophthalimide(Compound no. 8-5)

[0082] A mixture of2-amino-6-chloro-4-fluoro-3-(tetrahydrophthalimido)phenol (0.31 g),cyclopentyl bromide (1.3 ml), potassium carbonate (0.14 g), andacetonitrile (5 ml) was heated under reflux for 2 hr. The solvent andexcess reagent were removed under reduced pressure. The residue waspurified by a silica gel column, eluted with ethyl acetate to give thetitle product (0.17 g).

EXAMPLE 26 Preparation of2-chloro-4-fluoro-5-(phthalimido)methoxybenzene

[0083] 4-Chloro-2-fluoro-5-methoxyaniline (10.0 g, 57 mmol) and phthalicanhydride (8.5 g, 57 mmol mmol) were dissolved in glacial acetic acid(200 ml) and the solution refluxed for 2 hr. Water was added and theresultant precipitate was separated by filtration. The residue waswashed with water and dried to afford the title compound (16.7 g); ¹HNMR (CDCl₃, 300 MHz) 3.89 (3H, s), 6.9 (1H, d, J=6.3 Hz), 7.33 (1H, d,J=9.0 Hz), 7.82 (2H, m), 7.97 (2H, m) ppm.

EXAMPLE 27 Preparation of6-chloro-4-fluoro-2-nitro-3-(phthalimido)methoxybenzene

[0084] 2-Chloro-4-fluoro-5-(phthalimido)methoxybenzene (5.0 g, 16.4mmol) was slowly added to a stirred mixture of con. sulfuric acid-con.nitric acid (10:1, 20 ml) at −20° C. Solution was then warmed to ambienttemperature and allowed to stir for 1 hr. Addition to ice-water resultedin a light yellow precipitate which was separated by filtration. Columnchromatography on silica gel in hexane-methylene chloride (3:7)furnished the title compound (3.2 g); ¹H NMR (CDCl₃, 300 MHz) 4.06 (3H,s), 7.54 (1H, d, J=8.5 Hz), 7.84 (2H, m), 7.97 (2H, m) ppm.

EXAMPLE 28 Preparation of3-chloro-5-fluoro-2-methoxy-6-(phthalimido)aniline

[0085] 6-Chloro-4-fluoro-2-nitro-3-(phthalimido)methoxybenzene (0.5 g,1.4 mmol) was dissolved in glacial acetic acid (5 ml) and reduced iron(0.32 g, 5.6 mmol) was added. The solution was stirred at ambienttemperature under a stream of nitrogen for 12 hr. Water was added andthe product extracted with ethyl acetate followed by washings withwater, brine, and drying (anhydrous sodium sulfate). Removal of thesolvent afforded the title compound (0.4 g); ¹H NMR (CDCl₃, 300 MHz)3.87 (3H,s), 4.21 (2H, br s), 6.65 (1H, d, J=9.4 Hz), 7.81 (2H, m), 7.95(2H, m) ppm.

EXAMPLE 29 Preparation of 4-chloro-6-fluoro-3-methoxy-2-nitroaniline

[0086] 3-Chloro-5-fluoro-2-methoxy-6-phthalimido)aniline (0.6 g, 1.7mmol) was dissolved in dimethylsulfoxide (3 ml) and anhydrous hydrazine(0.22 g, 6.8 mmol) was added. The solution was stirred at ambienttemperature for 12 hr under a stream of nitrogen. Water was added andthe product extracted with ether. The organic layer was washed withwater, dried (anhydrous sodium sulfate), and evaporated to furnish thetitle compound (0.22 g). ¹H NMR (CDCl₃, 300 MHz) 3.98 (3H, s), 5.09 (2H,br s), 7.2 (1H, d, J=10.5 Hz) ppm.

EXAMPLE 30 Preparation of 4-chloro-6-fluoro-3-methoxy-2-nitrophenylisocyanate

[0087] 4-Chloro-6-fluoro-3-methoxy-2-nitroaniline (0.5 g, 2.27 mmol) wasdissolved in anhydrous toluene (30 ml) and triethylamine (0.46 g, 4.54mmol) was added. This solution was slowly added to a stirred solution oftriphosgene (0.67 g, 2.27 mmol) in toluene (30 ml) and the solutionrefluxed for 2 hr. The solution was cooled and filtered. Clear filtratewas evaporated in vacuo to afford the title compound. ¹H NMR (CDCl₃,3.00 MHz) 3.96 (3H, s), 7.38 (1H, d, J=8.8 Hz) ppm.

EXAMPLE 31 Preparation of3-[4-chloro-6-fluoro-3-methoxy-2-nitrophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-5) from4-chloro-6-fluoro-3-methoxy-2-nitrophenyl isocyanate

[0088] Sodium hydride (0.06 g, 2.27 mmol) was suspended in 10 mlanhydrous dimethylformamide and to this was slowly added a solution ofethyl-3-amino-4,4,4-trifluorocrotonate (0.42 g, 2.27 mmol) in anhydroustoluene (10 ml). The solution was stirred for 15 min. until theevolution of hydrogen gas ceased. The solution was cooled to −30° C. anda solution of 4-chloro-6-fluoro-3-methoxy-2-nitrophenyl isocyanate (2.27mmol) in anhydrous toluene (10 ml) was slowly added with stirring. Thesolution was then allowed to warm to room temperature and methyl iodide(1.31 g, 9.1 mmol) was added. After stirring for 4 hr at ambienttemperature, water was added and product extracted with ethyl acetate.Column chromatography on silica gel in hexane:methylene chloride (4:6)afforded the title compound (0.13 g).

EXAMPLE 32 Preparation of 2-chloro-4-fluoro-5-(phthalimido)phenol

[0089] 5-Amino-2-chloro-4-fluorophenol (3.0 g, 18.6 mmol) and phthalicanhydride (3.3 g, 22.3 mmol) were dissolved in glacial acetic acid (60ml) and the solution refluxed for 2 hr. Water was added and theresultant precipitate was separated by filtration. The residue waswashed with water and dried to afford the title compound (5.04 g); ¹HNMR (CDCl₃ +CD ₃OD, 300 MHz) 3.68 (1H, s), 6.93 (1H, d, J=6.6 Hz), 7.27(1H, d, J=9.1 Hz), 7.84 (2H, dd, J=3.0, 5.5 Hz), 7.97 (2H, dd, J=3.0,5.5 Hz) ppm.

EXAMPLE 33 Preparation of6-chloro-4-fluoro-2-nitro-3-(phthalimido)phenol

[0090] 2-Chloro-4-fluoro-5-(phthalimido)phenol (5.0 g, 17.1 mmol) wasslowly added with stirring to con. nitric acid (50 ml) at −10° C.Solution was then warmed to ambient temperature and allowed to stir for0.5 hr. Addition to ice-water resulted in a light yellow precipitatewhich was separated by filtration to afford the title compound (5.5 g);¹H NMR (CDCl₃+CD₃OD, 300 MHz) 4.36 (1H, br s), 7.61 (1H, d, J=8.6 Hz),7.88 (2H, dd, J=3.0, 5.5 Hz), 7.99 (2H, dd, J=3.0, 5.5 Hz) ppm.

EXAMPLE 34 Preparation of 4-chloro-2,5-difluoronitrobenzene (XXXVIII)

[0091] 1-Chloro-2,5-difluorobenzene (31.7 g, 0.21 mol);was dissolved insulfuric acid (110 ml) at −40° C., then a solution of sulfuric acid (20ml) and nitric acid (30 ml) was added dropwise. The mixture was stirredfor 1 hr while temperature slowly raised to 20° C. The product wasforced to crystallize by mixing the reaction mixture with ice-water (500ml), the yellow crystals were filtered, washed with cold water and driedin fume hood overnight. (38.0 g). ¹H NMR (CDCl₃, 300 MHz) 7.46 (1H, dd,J=9.8, 9.9 Hz), 7.96 (1H, dd, J=7.9, 7.9 Hz) ppm.

EXAMPLE 35 Preparation of 4-chloro-2,5-difluoroaniline (XXXIX)

[0092] 1-Chloro-2,5-difluoro-4-nitrobenzene (XXXVIII) (17.5 g) wasdissolved in acetic acid (150 ml) in a 1 L 3-neck round bottom flaskequipped with cooling condenser. To it iron powder (35.0 g) was addedslowly while the solution was stirred by an overhead stirrer. Thereaction was exothermic which occurred in less than 30 min and generatedmuch heat that was absorbed by a cooling bath. After that, ethyl acetate(300 ml) was added and the mixture filtered. The solution was washedwith water and dried over sodium sulfate. The product was purified bycolumn chromatography (silica gel, hexane:ethyl acetate, 4:1) (14.3 g).¹H NMR (CDCl₃, 300 MHz) 3.89 (2H, br), 6.56 (1H, m), 7.02 (1H, m) ppm.

EXAMPLE 36 Preparation of ethyl 4-chloro-2,5-difluorophenylcarbamate(XL)

[0093] 4-Chloro-2,5-difluoroaniline (XXXIX) (2.1 g, 12.8 mmol) was mixedwith pyridine (20 ml) at 0° C., to it was dropwise added ethylchloroformate (1.5 g, 13.8 mmol). After stirring for 2.5 hr whiletemperature slowly raised to room temperature, pyridine was evaporatedand the residue crystallized in ice-water (100 ml). The crystals werefiltered, washed with water and dried in fume hood overnight (2.7 g). ¹HNMR (CDCl₃, 300 MHz) 1.33 (3H, t, J=7.1 Hz), 4.23 (2H, q, J=7.1 Hz),6.89 (1H, br), 7.12 (1H, dd, J=6.5, 6.5 Hz), 8.05 (1H, dd, J=7.8, 9.6Hz) ppm.

EXAMPLE 37 Preparation of ethyl4-chloro-3,6-difluoro-2-nitrophenylcarbamate (XLI)

[0094] Ethyl 4-chloro-2,5-difluorophenylcarbamate (XL) (2.4 g, 10.2mmol) was added to a mixture of sulfuric acid (12.5 ml) and nitric acid(0.8 ml) at −30° C. After stirring for 1.5 hr (−30° C. to r.t.), it waspoured into ice water (50 ml) and yellow crystals formed immediatelywhich were filtered, washed with water and dried in fume hood overnight(2.8 g). ¹H NMR (CDCl₃, 300 MHz) 1.30 (3H, t, J=7.1 Hz), 4.22 (2H, q,J=7.1 Hz), 6.97 (1H, br), 7.45 (1H, dd, J=6.3, 6.3 Hz) ppm.

EXAMPLE 38 Preparation of 4-chloro-3,6-difluoro-2-nitroaniline (V)

[0095] Ethyl 4-chloro-3,6-difluoro-2-nitrophenylcarbamate (XLI) (0.9 g,3.2 mmol) was mixed with acetic acid (30 ml) and hydrobromic acid (48%,25 ml), the mixture was stirred at 150° C. for 4 hr and then the volumereduced to half by evaporation. Ethyl acetate (50 ml) was added and thesolution was washed with water (15 ml×3) and dried over sodium sulfate.The product was purified by column chromatography (silica gel, hexane)(0.56 g). ¹H NMR (CDCl₃, 300 MHz) 5.73 (2H, br), 7.24 (1H, dd, J=6.1,6.1 Hz) ppm.

EXAMPLE 39 Preparation of3-(4-chloro-5-ethoxycarbonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (XLVII)

[0096] Ethyl chloroformate (2.58 g) was dropwise added into a solutionof 3-(5-amino-4-chloro-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (XLVI) in pyridine (25 ml) at 0° C., and stirred atroom temperature for one hr. The reaction mixture was diluted with ethylacetate, washed with 1N hydrochloric acid followed by water, and driedover sodium sulfate. After concentration, the crystals (5.46 g) werecollected by filtration. ¹H NMR (CDCl₃, 300 MHz) 1.31 (3H, t, J=7.1 Hz),4.22 (2H, q, J=7.1 Hz), 6.20 (1H, s), 7.14 (1H, br), 7.29 (1H, d, J=8.8Hz), 7.36 (1H, d, J=6.0 Hz), 8.26 (1H, bd, J=6.4 Hz) ppm.

EXAMPLE 40 Preparation of3-(4-chloro-3-ethoxycarbonylamino-6-fluoro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-33)

[0097]3-(4-Chloro-5-ethoxycarbonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (XLVII) (1.0 g) was stirred with sulfuric acid (2ml) at 0° C., then a mixture of nitric acid (1 ml) and sulfuric acid (1ml) was dropwise added. After stirring at room temperature for 3 hr, itwas poured into ice water (50 ml) and yellow crystals formed immediatelywhich was filtered, washed with water and dried in fume hood overnight(0.5 g).

EXAMPLE 41 Preparation of3-(4-chloro-3-ethoxycarbonylamino-6-fluoro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 1-34)

[0098]3-(4-chloro-3-ethoxycarbonylamino-6-fluoro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.96 g) was stirred with dimethyl sulfate (0.72 ml)and potassium carbonate (0.33 g) in N,N-dimethylformamide (10 ml) atroom temperature overnight. The reaction mixture was diluted with ethylacetate, washed with water, dried over sodium sulfate, evaporated togive the title compound (1.1 g, oil).

EXAMPLE 42 Preparation of3-[4-chloro-6-fluoro3-methyl-2-(2-naphthoyl)aminophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-122)

[0099] Preparation of4-chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline

[0100] 4-Chloro-2-fluoro-5-methylaniline (5 g, 31.4 mmol) was dissolvedin tetrahydrofuran (100 ml) and potassium carbonate (6.0 g, 37.7 mmol)and phenyl chloroformate (5.9 g, 37.7 mmol) were added. Solution wasrefluxed for 3 hr and the solvent was removed under reduced pressure.Product was purified by column chromatography on silica gel (eluent,methylene chloride:hexane, 6:4; 7.15 g).

[0101] Preparation of4-chloro-2-fluoro-5-methyl-6-nitro-N-phenoxycarbonylaniline

[0102] 4-Chloro-2-fluoro-5-methyl-N-phenoxycarbonylaniline (7.1 g, 25.4mmol) was dissolved in chloroform (68 ml) and trifluoroaceticanhydride(13.5 ml) and ammoniun nitrate (2.4 g, 30.5 mmol) were slowly added withstirring at ambient temperature. The stirring was continued for 18 hrwhen a second batch of ammonium nitrate (0.4 g, 5 mmol) was added andstirring continued for 8 hr. Water was added and solution wasneutralized by slow addition of sodium bicarbonate solution followed byextraction with chloroform. Organic layer was dried and evaporated underreduced pressure to afford an oily product (8.5 g) which was used forthe next step without purification.

[0103] Preparation of3-(4-chloro-6-fluoro-3-methyl-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

[0104] Ethyl 3-amino-4,4,4-trifluorocrotonate (6.1 g, 33.1 mmol) wasdissolved in dimethylformamide (47 ml) and stirred at −10° C. To thissolution was slowly added 1,8-diazabicyclo[5.4.0]undec-7-ene (6.3 g,41.4 mmol) and solution stirred for 0.5 hr. To this solution was slowlyadded a solution of4-chloro-2-fluoro-5-methyl-6-nitro-N-phenoxycarbonylaniline (8.5 g) indimethylformamide (25 ml) followed by stirring at ambient temperaturefor 14 hr. Solution was then heated to 80° C. and stirred at thistemperature for 4 hr. Water was added and pH adjusted to 4 by additionof dilute hydrochloric acid. Product was extracted with ethyl acetatefollowed by evaporation of the solvent to afford the crude product (10.1g) which was subjected to N-methylation as follows.

[0105] Preparation of3-(4-chloro-6-fluoro-3-methyl-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

[0106]3-(4-Chloro-6-fluoro-3-methyl-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (10.1 g) was dissolved in dimethylformamide (100 ml)and potassium carbonate (5.7 g, 41.3 mmol) and dimethylsulfate (11.9 g,55.1 mmol) were added. Solution was stirred at ambient temperature for14 hr, water was added and product extracted with ethyl acetate. Thetitle compound was separated by column chromatography on silica gel(eluent, hexane-ethyl aceatate, 9:1; 8.5 g).

[0107] Preparation of3-(2-amino-4-chloro-6-fluoro-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

[0108]3-(4-Chloro-6-fluoro-3-methyl-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (2.0 g, 5.2 mmol) was dissolved in acetic acid (20ml) and iron powder (1.2 g, 21.5 mmol) was added. Solution was stirredat ambient temperature for 14 hr. Water was added and product extractedwith ethyl acetate followed by evaporation under reduced pressure. Titlecompound was separated by column chromatography on silica gel (eluent,hexane-ethyl acetate, 7:3; 1.5 g).

[0109] Preparation of3-[4-chloro-6-fluoro3-methyl-2-(2-naphthoyl)aminophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

[0110]3-(2-Amino-4-chloro-6-fluoro-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.5 g, 1.4 mmol) was dissolved in 1,4-dioxane (20ml) and triethyl amine (0.29 g, 2.9 mmol) and 2-naphthoyl chloride (0.41g, 2.2 mmol) were added. Solution was heated under reflux for 4 hr andsolvent removed under reduced pressure. Product was subjected to columnchromatography on silica gel and the title compound was eluted withhexane-ethyl acetate (8:2; 0.3 g).

EXAMPLE 43 Preparation ofN-[4-chloro-6-fluoro3-methoxy-2-(2-naphthoyl)aminophenyl]phthalimide(Compound no. 13-3)

[0111] 3-Chloro-5-fluoro-2-methoxy-6-(phthalimido)aniline (0.32 g, 1mmol), 2-naphthoyl chloride (0.23 g, 1.2 mmol), and triethyl amine (0.12g, 1.2 mmol) were dissolved in tetrahydrofuran (20 ml) and solutionrefluxed for 3 hr. Solvent was then removed under reduced pressure andthe residue subjected to column chromatography on silica gel. Titlecompound was eluted with hexane-ethyl acetate (7:3; 0.12 g).

EXAMPLE 44 Preparation of3-(2-amino-4-chloro-3-difluoromethoxy-6-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione ( Compound no. 1-38)

[0112]3-(2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.41 g, 4.0 mmol) and potassium carbonate (0.69 g,5.0 mmol) were suspended in dimethylformamide (50 ml) and stirred at 90°C. Chlorodifluoromethane was bubbled through the solution for 4 hr andwater was added. Product was extracted with ethyl acetate and subjectedto column chromatography (silica gel; eluent, methylenechloride-methanol, 99.5:0.5) to furnish the title compound (0.78 g).

EXAMPLE 45 Preparation of3-[4-chloro-6-fluoro-3-methyl-2-(phenoxycarbonylamino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 4-52)

[0113]3-(4-Chloro-6-fluoro-2-isocyanato-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

[0114]3-(2-Amino-4-chloro-6-fluoro-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.0 g, 2.9 mmol) and triethylamine (0.58 g, 5.7mmol) were dissolved in ethyl acetate (15 ml) and the solution wasslowly added to a solution of triphosgene (0.85 g, 2.9 mmol) in ethylacetate (15 ml). Solution was heated under reflux for 2 hr and filtered.Solvent was evaporated to afford the title compound as a residue whichwas used for the next step.

[0115]3-(4-Chloro-6-fluoro-3-methyl-2-phenoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

[0116]3-(4-Chloro-6-fluoro-2-isocyanato-3-methylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.4 mmol) and triethylamine (0.14 g, 1.4 mmol) weredissolved in toluene (15 ml) and the solution was treated with phenol(0.13 g, 1.4 mmol). Solution was stirred for 0.3 hr at ambienttemperature and water was added. Product was extracted with ethylacetate. Removal of the solvent followed by column chromatography onsilica gel (eluent, methylene chloride) afforded the title compound (0.3g).

EXAMPLE 46 Preparation of3-[4-chloro-6-fluoro-3-hydroxy-2-(2-naphthoylamnino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-114)

[0117]3-(2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.50 g, 1.4 mmol) and 2-naphthoyl chloride (0.27 g,1.4 mmol) were dissolved in 1,4-dioxane (10 ml) and the solution heatedunder reflux for 4 hr. Solvent was evaporated under reduced pressure andthe product purified by column chromatography on silica gel (eluent,hexane-ethyl acetate, 8:2) to furnish the title compound (0.60 g).

EXAMPLE 47 Preparation of3-[4-chloro-3-difluoromethoxy-6-fluoro-2-(2-naphthoylamino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-115)

[0118]3-[4-Chloro-6-fluoro-3-hydroxy-2-(2-naphthoylamino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.51 g, 1.0 mmol) dissolved in dimethylformamide (5ml) was slowly added to a stirred suspension of sodium hydride (0.03 g,1.3 mmol) in dimethylformamide (5 ml) at −10° C. Chlorodifluoromethanewas bubbled through the solution for 0.5 hr with stirring at −10° C.followed by addition of water. Product was extracted with ethyl acetateand solvent evaporated under reduced pressure. Residue was subjected otcolumn chromatography on silica gel (eluent, hexane-ether, 25:75) tofurnish the title compound (0.03 g).

EXAMPLE 48 Preparation of3-[4-chloro-2-(2-naphthoylamino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-131)

[0119] To a solution of triphosgene in anhydrous ethyl acetate (150 ml)was added dropwise a solution of 4-chloro-2-nitroaniline (10 g) andtriethylamine (12 g) in anhydrous ethyl acetate (50 ml) at 0° C. undernitrogen atmosphere. After addition, the resulting mixture was heated atreflux temperature for 1 hr, then allowed to cool to ambienttemperature. The precipitate was removed by filtration through Celiteand the filtrate was concentrated to give title compound as an brownsolid.

[0120] To a suspension of sodium hydride (60% dispersion in oil, 2.5 g)in anhydrous N,N-dimethylformamide (100 ml) was added dropwise asolution of ethyl-3-amino-4,4,4-trifluorocrotonate in toluene (50 ml) at0° C. under nitrogen atmosphere. After addition, the mixture was stirredfor 20 min at same temperature, then cooled to −30° C. A solution of(4-chloro-2-nitrophenyl)isocyanate in toluene (50 ml) was addeddropwise. After stirring for 20 min, the cold bath was removed and theresulting mixture was stirred overnight at ambient temperature. Thereaction mixture was partitioned between ethyl acetate and 1N-hydrochloric acid. The organic phase was washed with brine (×2) anddried over anhydrous sodium sulfate. The solvent was removed in vacuoand the residue was purified by column chromatography on silica geleluted with ethyl acetate and hexane (1:1) to afford3-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione(10.2 g).as a yellow solid.

[0121] Preparation of3-(4-chloro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

[0122] A mixture of 3-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (3 g), dimethyl sulfate (1.7 g) and potassiumcarbonate (1.85 g) in N,N-dimethylformamide (100 ml) was stirred at 55°C. overnight. The resulting mixture was allowed to cool to ambienttemperature and filtered through Celite to remove unsoluble precipitate.The filtrate was diluted with a mixed solvent of ethyl acetate andhexane (1:1, 200 ml), washed with brine (×2) and dried over anhydroussodium sulfate. After removal of the solvent, the residue wassolidified. The yellow solid was recrystallized from ethyl acetate andhexane to give desired compound ( 2.3 g).

[0123] Preparation of3-(2-amino-4-chlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

[0124] To a stirred suspension of3-(4-chloro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1 g) in methanol (20 ml), and conc. hydrochloricacid (10 ml) was added iron (powdered, 0.48 g) unded vigorous stirring.After addition, the mixture was heated at reflux temperature for 1 hr.The oil bath was removed and the solution was allowed to cool to ambienttemperature. Ethyl acetate (200 ml) was added, washed with brine (×2)and dried over anhydrous sodium sulfate. After removal of the solvent,the residue was purified by column chromatography on silica gel usingethyl acetate-hexane (1:3) as the eluent to give the title compound.

[0125] Preparation of3-[4-chloro-2-(2-naphthoylamino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-131)

[0126] A solution of3-(2-amino-4-chlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.4 g), 2-naphthoyl chloride (0.29 g) and triethylamine (0.19 g) in anhydrous tetrahydro furan (30 ml) was heated atreflux temperature overnight under nitrogen atmosphere. The reactionmixture was diluted with ethyl acetate (200 ml), washed with brine (×2)and dried over anhydrous sodium sulfate. The solvent was removed undedreduced pressure and the residue was purified by column chromatographyon silica gel using ethyl acetate and hexane (1:3) as the eluent give apale yellow solid. The solid was recrystallized from ethylacetate-hexane to give the title compound as a white crystal (0.42 g).

EXAMPLE 49 Preparation of3-[4-chloro-6-fluoro-2-(2-naphthoylamino)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-145)

[0127] A mixture of(2-amino-4-chloro-6-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.25 g), triethylamine (0.15 g) and 2-naphthoylchloride (0.21 g) in anhydrous tetrahydrofuran (30 ml) was heated atreflux temperature overnight under nitrogen atmosphere. The mixture waspoured into water and extracted with ethyl acetate. The organic layerwas washed with brine and dried over anhydrous sodium acetate. Thesolvent was removed in vacuo and the residue was purified by columnchromatography on silica gel using ethyl acetate-hexane (1:4) as theeluent to give the title compound as an white solid (0.26 g).

EXAMPLE 50 Preparation ofN-[4-chloro-2-(2-naphthoylamino)phenyl]phthalimide (Compound no. 13-5)

[0128] A reaction solution of N-(2-amino-4-chlorophenyl) phthalimide(0.5 g), triethylamine (0.28 g) and 2-naphthoyl chloride (0.35 g) inanhydrous tetrahydrofuran (50 ml) was heated at reflux temperature for 6hr under nitrogen atmosphere. The resulting mixture was poured intowater and extracted with ethyl acetate. The organic layer was washedwith brine (×2) and dried over anhydrous sodium sulfate. The solvent wasremoved and the residue was purified by column chromatography on silicagel using ethyl acetate-hexane(1 :5) to give the title compound (0.35 g)as a yellow solid.

EXAMPLE 51 Preparation of3-(2-benzylthioacetylamino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compoun no. 2-165)

[0129] A solution of benzylmercaptan (51.0 mg) in tetrahydrofuran (1.0ml) was slowly added to a suspension of sodium hydride (16.4 mg) intetrahydrofuran stirred under nitrogen at 0° C. The solution warmed toroom temperature over 20 minutes and tetrabutylammonium bromide (11 mg)was added. The suspension was cooled to −78° C. and a solution of3-(2-chloroacetylamino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione(150 mg) added. After stirring for a further 30minutes the mixture was allowed to warm to room temperature overnight.Water and ethyl acetate were added and the solution separated and theorganic phase was washed with water, brine and dried over sodiumsulfate. The solution was concentrated and chromatographed on silica geleluting with methylene chloride: ethyl acetate, 10:1, to give a whitesolid (137 mg).

EXAMPLE 52 Preparation of3-(2-aminocarbonylamino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 3-26)

[0130] A solution of the isocyanate (1 mM) in dioxane (20 ml), stirredat 0° C., was treated with a solution of 0.5 M ammonia in dioxane (3 mM)and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (3 drops). The solution wasallowed to warm to room temperature and stirred overnight.Chromatography on silica gel eluting with ethyl acetate gave the productas a yellow solid (271 mg).

EXAMPLE 53

[0131] Preparation of3-(4-chloro-6-fluoro-3-methoxy-2-thiomethylphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 17-1)

[0132] A solution of t-butylnitrile (73 mg) in methylene chloride (1 ml)was added to a stirred, ice cold solution of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (200 mg) and methyl disulfide (102 mg) in drymethylene chloride (4 ml). It was stirred at 0° C. for 1.5 h and allowedto warm to room temperature overnight. 1 N Hydrochloric acid was addedand the mixture extracted with ethyl acetate, washed with water, brineand dried over sodium sulfate. The solution was concentrated underreduced pressure and the residue chromatographed on silica gel elutingwith ethyl acetate : hexane, 5:1 gave the product as a yellow powder(189 mg).

EXAMPLE 54 Preparation of2-(4-chloro-6-fluoro-3-hydroxy-27nitrophenyl)-5-trifluoromethylpyridazin-3-one(Compound no. 11-2)

[0133] Nitric acid (70%, 12 ml) was added to the ice-cooled2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5-trifluoromethylpyridazin-3-one(1.25 g) and stirred at room temperature for 30 minutes. Crushed ice wasadded. The precipitate was collected by filtration and washed with waterto give 1.20 g of the desired product, m.p. 146-8° C.

EXAMPLE 55 Preparation of2-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-5-trifluoromethylpyridazin-3-one(Compound no. 11-3)

[0134] To a stirred solution of2-(4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl)-5-trifluoromethylpyridazin-3-one(0.601 g) in acetic acid (6 ml) was added 0.38 g of iron powder atambient temperature and stirred for 4 hours. The reaction mixture waspartitioned between ethyl acetate and water. The organic phase was driedover anhydrous sodium sulfate. After removing the solvent under reducedpressure, the residue was purified by silica gel column chromatography,eluted with hexane-ethyl acetate (2: 1) to give 0.515 g of the titlecompound.

EXAMPLE 56 Preparation of2-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-one(Compound no. 11-4) (BY715) and2-(4-chloro-6-fluoro-3-methoxy-2-methylaminophenyl)-5-trifluoromethylpyridazin-3-one(Compound no. 11-5)

[0135]2-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-one(0.515 g), methyl iodide (0.248 g), and potassium carbonate (0.219 g)were mixed in acetonitrile (10 ml) and heated at reflux for 2 hours. Thereaction mixture was partitioned between ethyl acetate and water. Theorganic phase was dried over anhydrous sodium sulfate. After removingthe solvent under reduced pressure, the residue was purified by silicagel column chromatography, eluted with hexane-ethyl acetate (4: 1) togive 0.40 g of2-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-one(Compound no. 11-4), m.p. 156-7° C. and2-(4-chloro-6-fluoro-3-methoxy-2-methylaminophenyl)-5-trifluoromethylpyridazin-3-one(Compound no.1 1-5)(7 mg).

EXAMPLE 57 Preparation of2-(4-chloro-6-fluoro-3-methoxy-2-naphthoylamidophenyl)-5-trifluoromethylpyridazin-3-one(Compound no. 11-6)

[0136]2-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-one(0.153 g) and 2-naphthoyl chloride (0.097 g) were mixed in dioxane (10ml) and heated at reflux for 5 hours. The reaction mixture waspartitioned between ethyl acetate and water. The organic phase was driedover anhydrous sodium sulfate. After removing the solvent under reducedpressure, the residue was purified by silica gel column chromatography,eluted with hexane-ethyl acetate (4: 1) to give 0.198 g of the titlecompound, m.p. 190-2° C.

EXAMPLE 58 Preparation of2-(2,4-dichloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-one(Compound no. 11-7) and2-[4-chloro-2-(2-chloro-2-ethoxycarbonylethyl)-6-fluoro-3-methoxyphenyl]-5-trifluoromethylpyridazin-3-one(Compound no. 11-8)

[0137] Copper(II) chloride (0.119 g), t-butyl nitrite (0.115 g), andethyl acrylate (3 ml) were placed in a flask, and cooled with a dryice-acetone bath at −65° C. To this mixture2-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-one(0.25 g) in acetonitrile (4 ml) was added and stirred. The reactionmixture was gradually warmed up to room temperature over night. Thereaction mixture was partitioned between ethyl acetate and water. Theorganic phase was dried over anhydrous sodium sulfate. After removingthe solvent under reduced pressure, the residue was purified by silicagel column chromatography, eluted with hexane-ethyl acetate (9:1) togive 0.077 g of2-(2,4-dichloro-6-fluoro-3-methoxyphenyl)-5-trifluoromethylpyridazin-3-oneand 0.033 g of2-[4-chloro-2-(2-chloro-2-ethoxycarbonylethyl)-6-fluoro-3-methoxyphenyl]-5-trifluoromethylpyridazin-3-one.

EXAMPLE 59 Preparation of2-(4-chloro-6-fluoro-3-hydroxy-2-naphthoylamidophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-194)

[0138] Boron tribromide-emthyl sulfide complex (5.15 g) was added to asolution of2-(4-chloro-6-fluoro-3-methoxy-2-naphthoylamidophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 1,2-dichloroethane (150 ml) and heated at refluxfor 1 hour. The reaction mixture was partitioned between methylenechloride and water. The organic phase was dried over anhydrous sodiumsulfate. After removing the solvent under reduced pressure, the residuewas purified by silica gel column chromatography, eluted withhexane-ethyl acetate (4:1 and 2:1) to give the title compound (4.127 g),m.p. 150-2° C.

EXAMPLE 60 Preparation of2-(4-chloro-3-ethoxy-6-fluoro-2-naphthoylamidophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 2-196)

[0139]2-(4-Chloro-6-fluoro-3-hydroxy-2-naphthoylamidophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.203 g), ethyl iodide (75 mg) and potassiumcarbonate (55 mg) were stirred in methylethyl ketone (9 ml) and dimethylsulfoxide (1 ml) at room temperature over night. The reaction mixturewas filtered and evaporated under reduced pressure. The residue waspurified by silica gel column chromatography, eluted with hexane-ethylacetate (4:1) to give the title compound (0.16 g).

EXAMPLE 61 Preparation of3-[4-chloro-2-diazanyl-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 15-1)

[0140]3-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.9 g, 2.4 mmol) was dissolved in conc.hydrochloric acid (5 ml) and the mixture cooled to −15° C., a solutionof NaNO₂ (0.2 g in 2 ml of H₂O) was added slowly. After stirred for 20min, a solution of SnCl₂•2H₂O (1.5 g in 4 ml of conc. hydrochloric acid)was added and the reaction continued at −15° C. for 30 min, then at roomtemperature for 30 min. The aqueous mixture was extracted with ethylacetate (5 ml×3) and the organic phase washed with brine and dried overNa₂SO₄. Column chromatography was used to purify the product (silicagel, hexane/ethyl acetate=6/4). Yield: 0.5 g, 1.3 mmol.

EXAMPLE 62 Preparation of3-[4-chloro-2-(2-cyclopropanecarbonyldiazanyl)-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 15-2)

[0141]3-[4-chloro-2-diazanyl-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.15 g, 0.4 mmol) was dissolved in dioxane (10 ml)and added with cyclopropanecarbonyl chloride (0.04 g, 0.4 mmol) andtriethylamine (0.04 g, 0.4 mmol). After stirred for 1 hr, the mixturewas poured into water (15 ml) and extracted with ethyl acetate (10ml×3). Organic phase was washed with brine and dried over Na₂SO4. Finalpurification involved column chromatography (silica gel, ether). Yield:0.15 g, 0.34 mmol.

EXAMPLE 63 Preparation of 3-{4-chloro-2-[2,2-(cyclopropylmethylene)diazanyl]-6-fluoro-3-methoxyphenyl}-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (Compound no. 15-11)

[0142]3-[4-chloro-2-diazanyl-6-fluoro-3-methoxyphenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.12 g, 0.31 mmol) was added to a methanol (10 ml)solution of cyclopropanecarboxaldehyde (0.024 g, 0.34 mmol) and themixture was stirred for 3 hr. After evaporation of solvent, the residuewas purified by column chromatography (silica gel, hexane/ether=3/2).Yield: 0.13 g, 0.31 mmol.

EXAMPLE 64 Preparation of3-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 16-6)

[0143] An acetonitrile (10 ml) solution of copper (II) sulfate (0.52 g,3.26 mmol), copper (I) oxide (0.47 g, 3.26 mmol) and copper (II) nitratehemipentahydrate (0.76 g, 3.26 mmol) was stirred at −30° C., and addedwith tert-butyl nitrite (0.41 g, 3.97 mmol) and then an acetonitrile (3ml) solution of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.94 g, 2.56 mmol). After stirred for 16 hr (−30°C. to room temperature), the mixture was poured into cold 5%hydrochloric acid (30 ml) and then extracted with ethyl acetate (20ml×3). The organic phase was washed with brine and dried over Na₂SO₄.Preparative TLC was used for purification (silica gel plates, 2000microns, ether). Yield: 0.16 g, 0.44 mmol.

EXAMPLE 65 Preparation of3-[4-chloro-6-fluoro-3-methoxy-2-(2-naphthoyloxy)phenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compound no. 16-7)

[0144]3-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.10 g, 0.27 mmol) was dissolved in dioxane (10ml) and the solution added with 2-naphthoyl chloride (0.062 g, 0.33mmol), triethylamine (0.033 g, 0.33 mmol). After stirred for 2 hr,solvent was evaporated and the residue purified by column chromatography(silica gel, hexane/ether=4/1). Yield: 0.12 g, 0.23 mmol.

EXAMPLE 66 Preparation of3-{4-chloro-2-[2-chloro-2-(ethoxycarbonyl)ethyl]-6-fluoro-3-methoxyphenyl}-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (Compounds no. 14-4 and 14-5)

[0145] A solution of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.94 g, 2.56 mmol) in acetonitrile (3 ml) wasslowly added to an acetonitrile (9 ml) solution of ethyl acrylate (6ml), tert-butyl nitrite (0.41 g, 3.97 mmol), and copper (II) chloride(0.42 g, 3.12 mmol) at −20° C. After stirred for 16 hr (−20° C. to roomtemperature), the mixture was poured into cold 5% hydrochloric acid (30ml) and extracted with ethyl acetate (20 ml×3), the organic phase waswashed with cold 5% NaHCO₃ and brine, dried over Na₂SO₄. Columnchromatography was used for purification (silica gel, hexane/ether=9/1)which also isolated two isomers. Yield: isomer-I (eluted earlier), 0.23g, 0.47 mmol; isomer-2 (eluted later), 0.14 g, 0.29 mmol.

[0146] Using the procedures as described in Schemes 1-17 and Examples1-66, the compounds of this invention can be readily prepared. TablesI-XVII list structures for few representative compounds of thisinvention. TABLE I

No. X Y W R₁ R₂ R₃ R₄ R₅ R₈ R₉ 1-1 Cl F OCH₃ H CF₃ H O O O O 1-2 Cl F OHH CF₃ H O O O O 1-3 Cl F OCH₃ H CF₃ H H H O O 1-4 Cl F OCH₃ CH₃ CF₃ H HH O O 1-5 Cl F OCH₃ CH₃ CF₃ H O O O O 1-6 Br F OH CH₃ CF₃ H O O O O 1-7Br F OCH₃ CH₃ CF₃ H H H O O 1-8 Br F OH CH₃ CF₃ H H H O O 1-9 Cl F OCH₃CH₃ CF₃ NO₂ O O O O 1-10 Cl F OCH₃ CH₃ CF₃ NH₂ H H O O 1-11 Cl F OCH₃CH₃ CF₃ H CH₃ CH₃ O O 1-12 Cl F OCH₃ NH₂ CF₃ H O O O O 1-13 Cl F OCH₃NH₂ CF₃ H H H O O 1-14 Cl F OCH₃ C₂H₅ CF₃ H O O O O 1-15 Cl F OCH₃ C₂H₅CF₃ H H H O O 1-16 Cl F OH CH₃ CF₃ H H H O O 1-17 Cl F OH CH₃ CF₃ H O OO O 1-18 Cl F OCH₂CN CH₃ CF₃ H H H O O 1-19 Cl F propargyloxy CH₃ CF₃ HH H O O 1-20 Cl F OCH₂CH═CHCOOCH₃ CH₃ CF₃ H H H O O 1-21 Cl Fcyclopentyloxy CH₃ CF₃ H H H O O 1-22 Cl F benzyloxy CH₃ CF₃ H H H O O1-23 Cl F 3-nitro-2-pyridyloxy CH₃ CF₃ H H H O O 1-24 Cl F OCH₃ CH₃ CHF₂H H H O O 1-25 Cl F OCH₃ CH₃ CF₃ Cl H H O O 1-26 Cl F OCH₃ CH₃ CF₃ H H HS O 1-27 Cl F OCH₃ CH₃ CF₃ H H H O S 1-28 CN F OCH₃ CH₃ CF₃ H H H O O1-29 Cl H OCH₃ CH₃ CF₃ H H H O O 1-30 Cl F OCH₃ CH₃ CF₃ H ═C(CCl₃)Cl O O1-31 Cl F OCH₃ CH₃ CF₃ H ═C(H)N(CH₃)₂ O O 1-32 Cl F OCH₃ CH₃ CF₃ H—(CH₂)₄— O O 1-33 Cl F NHCOOCH₂CH₃ H CF₃ H O O O O 1-34 Cl F NHCOOCH₂CH₃CH₃ CF₃ H O O O O 1-35 Cl F CH₃ H CF₃ H O O O O 1-36 Cl F CH₃ CH₃ CF₃ HO O O O 1-37 Cl F CH₃ CH₃ CF₃ H H H O O 1-38 Cl F OCHF₂ CH₃ CF₃ H H H OO 1-39 Cl F OCH₂-2-naphthyl CH₃ CF₃ H H H O O 1-40 Cl F OCH₃ CH₃ CF₃ H—N—N— O O 1-41 H H H CH₃ CF₃ H H H O O 1-42 H H H CH₃ CF₃ H O O O O 1-43CN H H CH₃ CF₃ H O O O O 1-44 CN H H CH₃ CF₃ H H H O O 1-45 Cl Cl OH CH₃CF₃ H O O O O 1-46 OCH₃ F H CH₃ CF₃ H O O O O 1-47 Cl Cl OCH₃ CH₃ CF₃ HH H O O 1-48 OCH(CH₃)COOCH₂CH₃ H H CH₃ CF₃ H H H O O 1-49OCH(CH₃)COOCH₂CH₃ H H CH₃ CF₃ H O O O O 1-50 OCHF₂ F H CH₃ CF₃ H O O O O1-51 OCHF₂ F H CH₃ CF₃ H H H O O 1-52 CF₃ H H CH₃ CF₃ H O O O O 1-53OCHF₂ F H CH₃ CF₃ H CH(Me)CO₂Et H O O 1-54 Cl F H CH₃ CF₃ H CH(Me)CO₂EtH O O 1-55 Cl F OCH₃ CH₃ CF₃ H CH(Me)CO₂Et H O O 1-56 Cl F OH NH₂ CF₃ HH H O O 1-57 Cl F OCH₂CN NH₂ CF₃ H H H O O 1-58 Cl F OCH₂COOCH₃ NH₂ CF₃H H H O O 1-59 Cl F OCH₂COOCH₂CH₃ CH₃ CF₃ H H H O O 1-60 Cl FOCH(CH₃)COOCH₂CH₃ CH₃ CF₃ H H H O O 1-61 Cl F OCH₂CH₃ CH₃ CF₃ H H H O O1-62 Cl F OCH₂CH₃ CH₃ CF₃ H CH2CH3 H O O 1-63 Cl F OCH(CH₃)₂ CH₃ CF₃ H HH O O 1-64 Cl F OCH(CH₃)₂ CH₃ CF₃ H CH(CH3)2 H O O 1-65 Cl H H H CF₃ NO₂O O O O 1-66 Cl H OH CH₃ CF₃ H O O O O 1-67 Cl NO₂ OH CH₃ CF₃ H O O O O1-68 OCF₃ H H CH₃ CF₃ H O O O O 1-69 Cl NO₂ OCH₃ H CF₃ H O O O O 1-70 ClF F H CF₃ H O O O O 1-71 Cl H OH CH₃ CF₃ H H H O O 1-72 Cl H OCH₃ CH₃CF₃ H H H O O 1-73 OCF₃ H H CH₃ CF₃ H H H O O

[0147] TABLE II

No. X Y W R₁ R₂ R₃ R₄ R₅ R₈ R₉ 2-1 Cl F OCH₃ CH₃ CF₃ H COCH₃ H O O 2-2Cl F OCH₃ CH₃ CF₃ H COCH₃ COCH₃ O O 2-3 Cl F OCH₃ CH₃ CF₃ H CO-t-C₄H₉ HO O 2-4 Cl F OCH₃ CH₃ CF₃ H acryloyl acryloyl O O 2-5 Cl F OCH₃ CH₃ CF₃H methacryloyl H O O 2-6 Cl F OCH₃ CH₃ CF₃ H methacryloyl methacryloyl OO 2-7 Cl F OCH₃ CH₃ CF₃ H 3,3-dimethylacryloyl H O O 2-8 Cl F 0CH₃ CH₃CF₃ H 3,3-dimethylacryloyl 3,3- O O dimethylacryloyl 2-9 Cl F OCH₃ H CF₃H COCF₃ H O O 2-10 Cl F OCH₃ CH₃ CF3 H COCF₃ H O O 2-11 Cl F OCH₂CN CH₃CF₃ H COCF₃ H O O 2-12 Cl F OCH₃ CH₃ CF₃ NHCOCF₃ COCF₃ H O O 2-13 Cl FOCH₃ CH₃ CF₃ H COCH₂Cl H O O 2-14 Cl F OCH₃ CH₃ CF₃ H COCH₂CN H O O 2-15Cl F OCH₃ CH₃ CF₃ H COCOOCH₃ H O O 2-16 Cl F OCOCH₂COOCH₂CH₃ CH₃ CF₃ HCOCH₂COOCH₂CH₃ H O O 2-17 Cl F OCH₃ CH₃ CF₃ H c-C₃H₅-carbonyl H O O 2-18Cl F OCH₃ CH₃ CF₃ H c-C₃H₃-carbonyl c-C₃H₃- O O carbonyl 2-19 Cl F OCH₃CH₃ CF₃ H cyclohexanoyl H O O 2-20 Cl F OCH₃ CH₃ CF₃ H cyclohexanoylcyclohexanoyl O O 2-21 Cl F OCH₃ CH₃ CF₃ H SO₂CH₃ SO₂CH₃ O O Cl F OCH₃CH₃ CF₃ H SO₂CH₃ H O O 2-22 Cl F OCH₃ CH₃ CF₃ H benzoyl H O O 2-23 Cl FOCH₃ CH₃ CF₃ H 3-CH₃-benzoyl H O O 2-24 Cl F OCH₃ CH₃ CF₃ H4-CH₃-benzoyl H O O 2-25 Cl F OCH₃ CH₃ CF₃ H 4-CH₃-benzoyl 4-CH₃-benzoylO O 2-26 Cl F OCH₃ CH₃ CF₃ H 4-CH₃-benzenesulfonyl H O O 2-27 Cl F OCH₃CH₃ CF₃ H 4-C₂H₅-benzoyl H O O 2-28 Cl F OCH₂CN CH₃ CF₃ H 4-C₂H₅-benzoylH O O 2-29 Cl F OCH₃ CH₃ CF₃ H 4-n-C3H₇-benzoyl 4-n-C₃H₇- O O benzoyl2-30 Cl F OCH₃ CH₃ CF₃ H 4-t-C₄H₉-benzoyl H O O 2-31 Cl F OCH₃ CH₃ CF₃ H4-vinylbenzoyl H O O 2-32 Cl F OCH₃ CH₃ CF₃ H 3,4-(CH₃)₂-benzoyl H O O2-33 Cl F OCH₃ CH₃ CF₃ H 4-CF₃-benzoyl H O O 2-34 Cl F OCH₃ CH₃ CF₃ H4-CF₃-benzoyl 4-CF₃-benzoyl O O 2-35 Cl F OCH₃ CH₃ CF₃ H3,5-(CF₃)₂-benzoyl 3,5-(CF₃)₂- O O benzoyl 2-36 Cl F OCH₃ CH₃ CF₃ H4-CH₂Cl-benzoyl H O O 2-37 Cl F OCH₃ CH₃ CF₃ H 4-C₆H₅-benzoyl H O O 2-38Cl F OCH₃ CH₃ CF₃ H 4-C₆H₃-benzoyl 4-C₆H₅-benzoyl O O 2-39 Cl F OCH₃ CH₃CF₃ H 2-F-benzoyl H O O 2-40 Cl F OCH₃ CH₃ CF₃ H 4-F-beNzoyl H O O 2-41Cl F OCH₃ CH₃ CF₃ H 2,3-F₂-benzoyl H O O 2-42 Cl F OCH₃ CH₃ CF₃ H2,4-F₂-benzoyl H O O 2-43 Cl F OCH₃ CH₃ CF₃ H 2,4-F₂-benzoyl2,4-F₂-benzoyl O O 2-44 Cl F OCH₃ NH₂ CF₃ H 2,4-F₂-benzoyl H O O 2-45 ClF OCH₂CN CH₃ CF₃ H 2,4-F₂-benzoyl 2,4-F₂-benzoyl O O 2-46 Cl F OCH₃ CH₃CF₃ H 2,4-F₂-thiobenzoyl H O S 2-47 Cl F OCH₃ CH₃ CF₃ H 2,6-F₂-benzoyl HO O 2-48 Cl F OCH₃ CH₃ CF₃ H 3,4-F₂-benzoyl H O O 2-49 Cl F OCH₃ CH₃ CF₃H 3,4-F₂-benzoyl 3,4-F₂-benzoyl O O 2-50 Cl F OCH₃ CH₃ CF₃ H3,5-F₂-benzoyl H O O 2-51 Cl F OCH₃ CH₃ CF₃ H 3,5-F₂-benzoyl3,5-F₂-benzoyl O O 2-52 Cl F OCH₃ CH₃ CF₃ H 2,3,4,5,6-F₅-benzoyl H O O2-53 Cl F OCH₃ CH₃ CF₃ H 2-Cl-benzoyl H O O 2-54 Cl F OCH₃ CH₃ CF₃ H3-C1-benzoyl H O O 2-55 Cl F OCH₃ CH₃ CF₃ H 3-Cl-benzoyl 3-Cl-benzoyl OO 2-56 Cl F OCH₃ CH₃ CF₃ H 4-Cl-benzoyl H O O 2-57 Cl F OCH₃ CH₃ CF₃ H4-Cl-benzoyl 4-Cl-benzoyl O O 2-58 Cl F OCH₃ CH₃ CF₃ H 2,4-Cl₂-benzoyl HO O 2-59 Cl F OCH₃ CH₃ CF₃ H 3,4-Cl₂-benzoyl H O O 2-60 Cl F OCH₃ CH₃CF₃ H 3-Br-benzoyl 3-Br-benzoyl O O 2-61 Cl F OCH₃ CH₃ CF₃ H4-Br-benzoyl H O O 2-62 Cl F OCH₃ CH₃ CF₃ H 4-Br-benzoyl 4-Br-benzoyl OO 2-63 Cl F OCH₃ CH₃ CF₃ H 4- OCH₃-benzoyl H O O 2-64 Cl F OCH₃ CH₃ CF₃H 4-(OC₂H₅)-benzoyl H O O 2-65 Cl F OCH₃ CH₃ CF₃ H 4-(OC₂H₅)-benzoyl4-(OC₂H₅)- O O benzoyl 2-66 Cl F OCH₃ CH₃ CF₃ H 4-I-benzoyl H O O 2-67Cl F OCH₃ CH₃ CF₃ H 4-CN-benzoyl H O O 2-68 Cl F OCH₃ CH₃ CF₃ H4-N(CH₃)₂-benzoyl H O O 2-69 Cl F OCH₃ CH₃ CF₃ H 4-NO₂-benzoyl4-NO₂-benzoyl O O 2-70 Cl F OCH₃ CH₃ CF₃ H 3,5-(NO₂)₂-benzoyl H O O 2-71Cl F OCH₃ CH₃ CF₃ H 4-OCF₃benzoyl 4-OCF₃- O O benzoyl 2-72 Cl F OCH₃ CH₃CF₃ H 4-OCF₃-benzoyl H O O 2-73 Cl F OCH₃ CH₃ CF₃ H piperonyloyl H O O2-74 Cl F OCH₃ CH₃ CF₃ H 1-naphthoyl H O O 2-75 Cl F OCH₃ CH₃ CF₃ H2-naphthoyl H O O 2-76 Cl F OCH₃ H CF₃ H 2-naphthoyl H O O 2-77 Cl FOCH₃ NH₂ CF₃ H 2-naphthoyl H O O 2-78 Cl F OCH₃ CH₃ CF₃ H cinnamoyl H OO 2-79 Cl F OCH₃ CH₃ CF₃ H 2,4-F₂-cinnamoyl H O O 2-80 Cl F OCH₃ CH₃ CF₃H 2-methylcinnamoyl H O O 2-81 Cl F OCH₃ CH₃ CF₃ H α-methylcinnamoyl H OO 2-82 Cl F OCH₃ CH₃ CF₃ H 2-chlorocinnamoyl H O O 2-83 Cl F OCH₃ CH₃CF₃ H 2-chlorocinnamoyl 2- O O chlorocinnamoyl 2-84 Cl F OCH₃ CH₃ CF₃ H4-chlorocinnamoyl H O O 2-85 Cl F OCH₃ CH₃ CF₃ H 4-methoxycinna-moyl H OO 2-86 Cl F OCH₃ CH₃ CF₃ H 3-phenylpropionyl H O O 2-87 Cl F OCH₂CN CH₃CF₃ H 3-phenylpropionyl H O O 2-88 Cl F OCH₃ CH₃ CF₃ H 4-phenylbutyryl HO O 2-89 Cl F OCH₃ CH₃ CF₃ H COCH₂OCH₂C₆H₅ H O O 2-90 Cl F OCH₃ CH₃ CF₃H 2-furoyl H O O 2-91 Cl F OCH₃ CH₃ CF₃ H 3-CH₃-2-furoyl H O O 2-92 Cl FOCH₃ CH₃ CF₃ H furylacryloyl H O O 2-93 Cl F OCH₃ CH₃ CF₃ HCOCH₂-(2-thiophene) H O O 2-94 Cl F OH CH₃ CF₃ H 3-CH₃-2-thiophenoyl H OO 2-95 Cl F OCH₃ CH₃ CF₃ H 5-CH₃-2-thiophenoyl H O O 2-96 Cl F OCH₃ CH₃CF₃ H 5-CH₃-2-thiophenoyl 5-CH₃-2- O O thiophenoyl 2-97 Cl F OCH₃ CH₃CF3 H thiophene-2-carbonyl thiophene-2- O O carbonyl 2-98 Cl F OCH₃ CH₃CF₃ H 3-pyridoyl H O O 2-99 Cl F OCH₃ CH₃ CF₃ H 4-pyridoyl H O O 2-100Cl F OCH₃ CH₃ CF₃ H 2-Cl-5-pyridoyl 2-Cl-5- O O pyridoyl 2-101 Cl F OHCH₃ CF₃ H 3-NO₂-2-pyridoyl H O O 2-102 Cl F OH CH₃ CF₃ H 2-pyrimidoyl HO O 2-103 Cl F OCH₃ CH₃ CF₃ H benzothiophene-2- H O O carbonyl 2-104 ClF OCH₃ CH₃ CF₃ H 2-quinoyl H O O 2-105 Cl F OCH₃ CH₃ CF₃ H 2-quinoxaloylH O O 2-106 Br F OCH₃ CH₃ CF₃ H 2,4-F₂-benzoyl H O O 2-107 Cl F OCH₃ CH₃CHF₂ H 2,4-F₂-benzoyl H O O 2-108 Cl F OCH₃ CH₃ CF₃ Cl 2,4-F₂-benzoyl HO O 2-109 Cl F OCH₃ CH₃ CF₃ H 2,4-F₂-benzoyl H S O 2-110 Cl F OCH₃ CH₃CF₃ H 2,4-F₂-benzoyl H O S 2-111 CN F OCH₃ CH₃ CF₃ H 2,4-F₂-benzoyl H OO 2-112 Cl H OCH₃ CH₃ CF₃ H 2,4-F₂-benzoyl H O O 2-113 Cl F OCH₃ CH₃ CF₃H 3-(2-thienyl)acryloyl H O O 2-114 Cl F OH CH₃ CF₃ H 2-naphthoyl H O O2-115 Cl F OCHF₂ CH₃ CF₃ H 2-naphthoyl H O O 2-116 Cl F OCH₃ CH₃ CF₃ HCOCH₂OCOCH₃ COCH₂OCOCH₃ O O 2-117 Cl F OCH₃ CH₃ CF₃ H COCH₂OCOCH₃ H O O2-118 Cl F OCH₃ CH₃ CF₃ H COCOOCH₂CH₃ H O O 2-119 Cl F OCH₃ CH₃ CF₃ HCOCH₂OC₆H₅ H O O 2-120 Cl F OCH₃ CH₃ CF₃ H COCH₂OC₆H₅ COCH₂OC₆H₅ O O2-121 Cl F OCH₃ CH₃ CF₃ H COCOC₆H₅ H O O 2-122 Cl F CH₃ CH₃ CF₃ H2-naphthoyl H O O 2-123 Cl F CH₃ CH₃ CF₃ H cinnamoyl H O O 2-124 Cl FOCH₃ CH₃ CF₃ H CO-2,6-dimethylphenyl H O O 2-125 Cl F OCH₃ CH₃ CF₃ H2-F-cinnamoyl H O O 2-126 Cl F OCH₃ CH₃ CF₃ H 2-nitro-cinnamoyl H O O2-127 Cl F OCH₃ CH₃ CF₃ H 2-methoxy-cinnamoyl H O O 2-128 Cl F OCH₃ CH₃CF₃ H 2,6-dichloro-cinnamoyl H O O 2-129 Cl F OCH₃ CH₃ CF₃ H COCH₂CH₂-2-H O O methylphenyl 2-130 Cl F OCH₃ CH₃ CF₃ H COCH₂CH₂-2,5- H O Odimethylphenyl 2-131 Cl H H CH₃ CF₃ H 2-naphthoyl H O O 2-132 Cl F OCH₃CH₃ CF₃ H COCH₂CH₂-2,5- H O O dimethylphenyl 2-133 Cl F OCH₃ CH₃ CF₃ HCOCH₂O-4-F-phenyl H O O 2-134 Cl F OCH₃ CH₃ CF₃ H 3-chlorocinnamoyl H OO 2-135 Cl F OCH₃ CH₃ CF₃ H COCH₂O-4-Cl-phenyl H O O 2-136 Cl F OCH₃ CH₃CF₃ H α-cyano-cinnamoyl H O O 2-137 Cl H H CH₃ CF₃ H cinnamoyl H O O2-138 CN H H CH₃ CF₃ H O O O O 2-139 H H H CH₃ CF₃ H 2-naphthoyl2-naphthoyl O O 2-140 CN H H CH₃ CF₃ H 2-naphthoyl H O O 2-141 CN H HCH₃ CF₃ H cinnamoyl H O O 2-142 H H H CH₃ CF₃ H 2-naphthoyl H O O 2-143OCH₃ H H CH₃ CF₃ H 2-naphthoyl H O O 2-144 Cl Cl OCH₃ CH₃ CF₃ H2-naphthoyl H O O 2-145 Cl F H CH₃ CF₃ H 2-naphthoyl H O O 2-146OCH(CH₃)COOCH₂CH₃ H H CH₃ CF₃ H 2-naphthoyl H O O 2-147 Cl F H CH₃ CF₃ Hcyclopropyl H O O 2-148 OCHF₂ F H CH₃ CF₃ H 2-naphthoyl H O O 2-149 CF₃H H CH₃ CF₃ H 2-naphthoyl H O O 2-150 Cl F OH CH₃ CF₃ H phenylacetyl H OO 2-151 Cl F OCH₃ CH₃ CF₃ H phenylacetyl H O O 2-152 Cl F OCH₃ CH₃ CF₃ H3-methoxy- H O O 2-naphthoyl 2-153 Cl F OCH₃ CH₃ CF₃ H 1-methoxy- H O O2-naphthoyl 2-154 Cl F OCH₃ CH₃ CF₃ H 2,4-dichloro- H O O phenoxyacetyl2-155 Cl F OCH₃ CH₃ CF₃ H 3-methyl-2-naphthoyl H O O 2-156 Cl F OCH₃ CH₃CF₃ H 6-methyl-2-naphthoyl H O O 2-157 Cl F OCH₃ CH₃ CF₃ H3-chloro-2-naphthoyl H O O 2-158 Cl F OCH₃ CH₃ CF₃ H 5-bromo-2-naphthoylH O O 2-159 Cl F OCH₃ CH₃ CF₃ H 4-bromo-2-naphthoyl H O O 2-160 Cl FOCH₃ CH₃ CF₃ H 4-bromo-2-naphthoyl 4-bromo-2- O O naphthoyl 2-161 Cl FOCH₃ CH₃ CF₃ H 8-fluoro-2-naphthoyl H O O 2-162 Cl F OCH₃ CH₃ CF₃ H5-chloro-2-naphthoyl H O O 2-163 Cl F OCH₃ CH₃ CF₃ H 5-cyano-2-naphthoylH O O 2-164 Cl F OCH₃ CH₃ CF₃ H chloroacetyl H O O 2-165 Cl F OCH₃ CH₃CF₃ H benzylthioacetyl H O O 2-166 Cl F OCH₃ CH₃ CF₃ H bromoacetyl H O O2-167 Cl F OCH₃ CH₃ CF₃ H phenylthioacetyl H O O 2-168 Cl F OCH₃ CH₃ CF₃H methylthioacetyl H O O 2-169 Cl F OCH₃ CH₃ CF₃ H 2-naphthylthio-acetylH O O 2-170 Cl F OCH₃ CH₃ CF₃ H ethoxycarbonyl- H O O methylthioacetyl2-171 Cl F OCH₃ CH₃ CF₃ H ethoxycarbonyl-ethyl-2- H O O thioacetyl 2-172Cl F OCH₃ CH₃ CF₃ H ethylthioacetyl H O O 2-173 Cl F OCH₃ CH₃ CF₃ Hi-propylthioacetyl H O O 2-174 Cl F OCH₃ CH₃ CF₃ H propylthioacetyl H OO 2-175 Br F OCH₃ CH₃ CF₃ H 2-cinnamoyl H O O 2-176 Br F OCH₃ CH₃ CF₃ H2-cinnamoyl 2-cinnamoyl O O 2-177 Br F OCH₃ CH₃ CF₃ H 2-cinnamoyl H O O2-178 Br F OCH₃ CH₃ CF₃ H 2-cinnamoyl 2-cinnamoyl O O 2-179 CN F OCH₃CH₃ CF₃ H 2-cinnamoyl H O O 2-180 CN F OCH₃ CH₃ CF₃ H 2-naphthoyl H O O2-181 CN F OCH₃ CH₃ CF₃ H 2-naphthoyl H O O 2-182 Br F OCH₃ CH₃ CF₃ H4-vinylbenzoyl H O O 2-183 Br F OCH₃ CH₃ CF₃ H 4-vinylbenzoyl4-vinylbenzoyl O O 2-184 Cl F OCH₃ NH₂ CF₃ H 2-naphthoyl H O O 2-185 ClF OCH₃ NH₂ CF₃ H 2-cinnamoyl H O O 2-186 Cl F OCH₃ NH₂ CF₃ H 2-cinnamoyl2-cinnamoyl O O 2-187 Cl F OCH₃ NH₂ CF₃ H benzyloxyacetyl H O O 2-188 ClF OCH₂CN NH₂ CF₃ H 2-naphthoyl H O O 2-189 Cl F OCH₂COOCH₂CH₃ CH₃ CF₃ H2-naphthoyl H O O 2-190 Cl F OCH₂COOCH₂CH₃ CH₃ CF₃ H 2-cinnamoyl H O O2-191 Cl F OCH(CH₃)COOCH₂CH₃ CH₃ CF₃ H 2-naphthoyl H O O 2-192 Cl F OHNH₂ CF₃ H 2-naphthoyl H O O 2-193 4-CF₃- H H CH₃ CF₃ H 2-naphthoyl H O Opyridyloxy 2-194 Cl F OH CH₃ CF₃ H 2-naphthoyl H O O 2-195 Cl F OCH₂C≡CHCH₃ CF₃ H 2-naphthoyl H O O 2-196 Cl F OCH₂CH₃ CH₃ CF₃ H 2-naphthoyl H OO 2-197 Cl F OCH(CH₃)₂ CH₃ CF₃ H 2-naphthoyl H O O 2-198 Cl F OCH₃ CH₃CF₃ H Hexanoyl H O O 2-199 Cl F 3-NO₂- CH₃ CF₃ H 2-naphthoyl H O Opyridyloxy 2-200 Cl F OCH₂CN CH₃ CF₃ H 2-naphthoyl H O O 2-201 CH₃ H HCH₃ CF₃ H 2-naphthoyl H O O 2-202 Cl H OCH₃ CH₃ CF₃ H 2-naphthoyl H O O2-203 OCF₃ H H CH₃ CF₃ H 2-naphthoyl H O O 2-204 Cl H H CH₃ CF₃ Hc-C₃H₅-carbonyl H O O 2-205 H₂NC(S) H H CH₃ CF₃ H 2-naphthoyl H O O2-206 Cl F OCH₃ CH₃ CF₃ H c-C₃H₅-carbonyl H O O 2-207 COOCH₃ H H CH₃ CF₃H 2-naphthoyl H O O

[0148] TABLE III

No. X Y R R₁ R₂ R₃ R₄ R₅ R₈ R₉ 3-1 Cl F CH₃ CH₃ CF₃ H CONHCH₃ CONHCH₃ OO 3-2 Cl F CH₃ CH₃ CF₃ H CONHCH₂CH₂CH₃ H O O 3-3 Cl F CH₃ CH₃ CF₃ HCON[CH(CH₃)₂]₂ H O O 3-4 Cl F CH₃ CH₃ CF₃ H CONHC₆H₅ H O O 3-5 Cl F CH₃CH₃ CF₃ H CON(CH₃)C₆H₅ H O O 3-6 Cl F CH₃ CH₃ CF₃ H CONHCH_(2C) ₆H₅ H OO 3-7 Cl F CH₃ CH₃ CF₃ H CONHCH(CH₃)-C₆H₅ H O O 3-8 Cl F CH₃ CH₃ CF₃ HCON(CH₃)CH₂C₆H₅ H O O 3-9 Cl F CH₃ CH₃ CF₃ H CONHCH₂-(4-CH₃)phenyl H O O3-10 Cl F CH₃ CH₃ CF₃ H CONH CH₂-2,4-F₂-phenyl H O O 3-11 Cl F CH₃ CH₃CF₃ H CONH CH₂CH₂C₆H₅ H O O 3-12 Cl F CH₃ CH₃ CF₃ H CONH CH₂CH₂CH₂C₆H₅ HO O 3-13 Cl F CH₃ CH₃ CF₃ H CONH-2-naphthoyl H O O 3-14 Cl F CH₂CN CH₃CF₃ H CONHCH₂C₆H₅ H O O 3-15 Cl F CH₃ H CF₃ H CONHCH₂C₆H₅ H O O 3-16 ClF CH₃ NH₂ CF₃ H CONHCH₂C₆H₅ H O O 3-17 Cl F CH₃ CH₃ CHF₂ H CONHCH₂C₆H₅ HO O 3-18 Cl F CH₃ CH₃ CF₃ Cl CONHCH₂C₆H₅ H O O 3-19 Cl F CH₃ CH₃ CF₃ HCONHCH₂C₆H₅ H S O 3-20 Cl F CH₃ CH₃ CF₃ H CONHCH₂C₆H₅ H O S 3-21 CN FCH₃ CH₃ CF₃ H CONHCH₂C₆H₅ H O O 3-22 Cl H CH₃ CH₃ CF₃ H CONHCH₂C₆H₅ H OO 3-23 Cl F CH₃ CH₃ CF₃ H CON(C₆H₅)CH₂C₆H₅ H O O 3-24 Cl F CH₃ CH₃ CF₃ HCONHCH(C₆H₅)C₆H₅ H O O 3-26 Cl F CH₃ CH₃ CF₃ H CONH₂ H O O

[0149] TABLE IV

No. X Y W R₁ R₂ R₃ R₄ R₅ R₈ R₉ 4-1 Cl F OCH₃ CH₃ CF₃ H COOCH₃ H O O 4-2Cl F OCH₃ CH₃ CF₃ H COOCH₃ COOCH₃ O O 4-3 Cl F OCH₃ CH₃ CF₃ H COO-phenylH O O 4-4 Cl F OCH₃ CH₃ CF₃ H COO-[2,4-(CH₃)₂]-phenyl H O O 4-5 Cl FOCH₃ CH₃ CF₃ H COOCH₂-phenyl H O O 4-6 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(2-F)-phenyl H O O 4-7 Cl F OCH₃ CH₃ CF₃ H COOCH₂-(4-F)-phenyl HO O 4-8 Cl F OCH₃ CH₃ CF₃ H COOCH₂-(2-CF₃)-phenyl H O O 4-9 Cl F OCH₃CH₃ CF₃ H COOCH₂-(4-CF₃)-phenyl H O O 4-10 Cl F OCH₃ CH₃ CF₃ HCOO-2-naphthyl H O O 4-11 Cl F OCH₃ CH₃ CF₃ H COO-cyclohexyl H O O 4-12Cl F OCH₃ CH₃ CF₃ H COOCH₂-cyclohexyl H O O 4-13 Cl F OCH₃ CH₃ CF₃ HC(O)-S-phenyl H O O 4-14 Cl F OCH₂CN CH₃ CF₃ H COO-phenyl H O O 4-15 ClF OCH₃ H CF₃ H COO-phenyl H O O 4-16 Cl F OCH₃ NH₂ CF₃ H COO-phenyl H OO 4-17 Cl F OCH₃ CH₃ CHF₂ H COO-phenyl H O O 4-18 Cl F OCH₃ CH₃ CF₃ ClCOO-phenyl H O O 4-19 Cl F OCH₃ CH₃ CF₃ H COO-phenyl H S O 4-20 Cl FOCH₃ CH₃ CF₃ H COO-phenyl H O S 4-21 CN F OCH₃ CH₃ CF₃ H COO-phenyl H OO 4-22 Cl H OCH₃ CH₃ CF₃ H COO-phenyl H O O 4-23 Cl F OCH₂CN CH₃ CF₃ HCOOCH₂-phenyl H O O 4-24 Cl F OCH₃ CH₃ CF₃ H COOCH₂-(2,6-di-Cl)-phenyl HO O 4-25 Cl F OCH₃ CH₃ CF₃ H COO-[2,4,6-(CH₃)₃]-phenyl H O O 4-26 Cl FOCH₃ CH₃ CF₃ H COOCH₂-[3,4-(CH₃)₂- H O O phenyl 4-27 Cl F OCH₃ CH₃ CF₃ HCOO-(2-t-butyl)-phenyl H O O 4-28 Cl F OCH₃ CH₃ CF₃ H COOCH₂-2-naphthylH O O 4-29 Cl F OCH₃ CH₃ CF₃ H COOCH₂-(2,6-di-F)-phenyl H O O 4-30 Cl FOCH₃ CH₃ CF₃ H COOCH₂-(3,4-di-F)-phenyl H O O 4-31 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(4-ethyl)-phenyl H O O 4-32 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(3,4-di-Cl)-phenyl H O O 4-33 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(2-CF₃)-phenyl H O O 4-34 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(2-NO₂)-phenyl H O O 4-35 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(2-OCH₃)-phenyl H O O 4-36 Cl F OCH₃ CH₃ CF₃ H COOCH₂-2-pyridyl HO O 4-37 Cl F OCH₃ CH₃ CF₃ H COOCH₂-[3,5-(CH₃)₂]- H O O phenyl 4-38 Cl FOCH₃ CH₃ CF₃ H COOCH₂-[2,5-(CH₃)₂]- H O O phenyl 4-39 Cl F OCH₃ CH₃ CF₃H COOCH₂-(2,5-di-F)-phenyl H O O 4-40 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(4-OCH₃)-phenyl H O O 4-41 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(3,4-OCH₂O)- H O O phenyl 4-42 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(4-i-C₃H₇)-phenyl H O O 4-43 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(4-CF₃)-phenyl H O O 4-44 Cl F OCH₃ CH₃ CF₃ H COOCH₂-(3-F)-phenylH O O 4-45 Cl F OCH₃ CH₃ CF₃ H COOCH₂-(4-OCF₃)-phenyl H O O 4-46 Cl FOCH₃ CH₃ CF₃ H COOCH-(c-C₃H₅)-phenyl H O O 4-47 Cl F OCH₃ CH₃ CF₃ HCOOCH(CH₃)-phenyl H O O 4-48 Cl F OCH₃ CH₃ CF₃ HCOOCH₂-(2,3,4,5,6-penta- H O O F)-phenyl 4-49 Cl H H CH₃ CF₃ HCOOCH₂-(2-F)-phenyl H O O 4-50 Cl H H CH₃ CF₃ H COO-phenyl H O O 4-51 ClF CH₃ CH₃ CF₃ H COOCH₂-(2-F)-phenyl H O O 4-52 Cl F CH₃ CH₃ CF₃ HCOO-phenyl H O O 4-53 Cl F CH₃ CH₃ CF₃ H COO-3,4-dimethylphenyl H O O4-54 Cl F CH₃ CH₃ CF₃ H COOCH₂-2-Cl-phenyl H O O 4-55 Cl F CH₃ CH₃ CF₃ HCOO-2,6-dimethylpheny H O O 4-56 Cl F CH₃ CH₃ CF₃ HCOOCH₂-2-methylphenyl H O O 4-57 Cl F CH₃ CH₃ CF₃ H COOCH₂CH₂-phenyl H OO 4-58 Cl F CH₃ CH₃ CF₃ H COOCH₂-2-methoxyphenyl H O O 4-59 Cl F CH₃ CH₃CF₃ H COO-2,6-dimethoxyphenyl H O O 4-60 Cl F CH₃ CH₃ CF₃ HCOOCH₂-4-methylphenyl H O O 4-61 Cl F CH₃ CH₃ CF₃ H COOCH₂-4-Cl-phenyl HO O 4-62 Cl F CH₃ CH₃ CF₃ H COOCH₂-2,4- H O O dichlorophenyl 4-63 Cl FCH₃ CH₃ CF₃ H COOCH₂-3,4- H O O dimethoxyphenyl 4-64 Cl F CH₃ CH₃ CF₃ HCOOCH₂-4-nitrophenyl H O O 4-65 Cl F CH₃ CH₃ CF₃ HCOOCH₂-3-methoxyphenyl H O O 4-66 Cl F CH₃ CH₃ CF₃ H COSCH₂-phenyl H O O4-67 Cl F CH₃ CH₃ CF₃ H COOCH₂-3-nitrophenyl H O O 4-68 Cl F CH₃ CH₃ CF₃H COOCH₂-3-methylphenyl H O O 4-69 Cl F CH₃ CH₃ CF₃ H COOCH₂-2,4,6- H OO trimethylphenyl 4-70 Cl F CH₃ CH₃ CF₃ H COOCH₂-2-furanyl H O O

[0150] TABLE V

No. X Y R R₁ R₄ R₅ 5-1 Cl F CH₃ H O O 5-2 Cl F H H O O 5-3 Cl F CH₃(CH₂)₃F H H 5-4 Cl F H (CH₂)₃F O O 5-5 Cl F H (CH₂)₃F H H 5-6 Cl Cl CH₃H O O 5-7 Cl Cl CH₃ (CH₂)3_(F) O O 5-8 Cl Cl H (CH₂)₃F O O 5-9 Cl Cl H(CH₂)₃F H H 5-10 Cl F CH₃ (CH₂)₃F COCH₃ H 5-11 Cl F CH₃ (CH₂)₃F benzoylH 5-12 Cl F CH₃ (CH₂)₃F CH₃ CH3 5-13 Cl F CH₃ (CH₂)₃F COOCH₃ H 5-14 Cl FCH₃ (CH₂)₃F CONHCH₃ H 5-15 Cl Cl CH₂C≡CH (CH₂)₃F H H 5-16 Cl Cl CH(CH₃)₂(CH₂)₃F H H 5-17 Cl F CH₂C≡CH (CH₂)₃F H H 5-18 Cl F CH(CH₃)₂ (CH₂)₃F H H5-19 CN F CH₃ (CH₂)₃F benzoyl H 5-20 Cl H CH₃ (CH₂)₃F benzoyl H 5-21 ClF CH₃ (CH₂)₃F 2,4-F₂-benzoyl H 5-22 Cl F CH₃ (CH₂)₃F 4-C₂H₅-benzoyl H5-23 Cl F CH₃ (CH₂)₃F 3-phenyl- H propionyl 5-24 Cl F CH₂CN (CH₂)₃F2,4-F₂-benzoyl H 5-25 Cl F CH₂CN (CH₂)₃F 2-naphthoyl H 5-26 Cl F CH₃(CH₂)₃F 2-naphthoyl H 5-27 Cl F CH₃ (CH₂)₃F 2-naphthoyl 2-naphthoyl 5-28Cl F CH₃ (CH₂)₃F benzyloxyacetyl H

[0151] TABLE VI

No. X Y W R₁ R₂ R₄ R₅ 6-1 Cl F OH CHF₂ CH₃ O O 6-2 Cl F OH CHF₂ CH₃ H H6-3 Cl F OCH₃ CHF₂ CH₃ H H 6-4 Cl F OCH₃ CHF₂ CH₃ COCH₃ H 6-5 Cl F OCH₃CHF₂ CH₃ benzoyl H 6-6 Cl Cl OCH₃ CHF₂ CH₃ CH₃ CH₃ 6-7 Cl Cl OCH₃ CHF₂CH₃ COOCH₃ H 6-8 Cl F OCH₃ CH₃ CH₃ benzoyl H 6-9 Cl F OCH₃ CHF₂ CH₂CH₃benzoyl H 6-10 Cl Cl OCH₃ CHF₂ CH₃ CONHCH₃ H 6-11 CN F OCH₃ CHF₂ CH₃benzoyl H 6-12 Cl H OCH₃ CHF₂ CH₃ benzoyl H 6-13 Cl Cl H CHF₂ CH₃2,4-difluoro- H benzoyl 6-14 Cl F OCH₃ CHF₂ CH₃ 2,4-difluoro- H benzoyl6-15 Cl F OCH₃ CHF₂ CH₃ 2-naphthoyl H 6-16 Cl Cl H CHF₂ CH₃ 2-naphthoylH 6-17 Cl Cl OCH₃ CHF₂ CH₃ 2-naphthoyl H 6-18 Cl Cl HNC(O)C₂H₅ CHF₂ CH₃O O 6-19 Cl Cl HNC(O)C₂H₅ CHF₂ CH₃ H H 6-20 Cl Cl NH₂ CHF₂ CH₃ H H 6-21Cl F H CHF₂ CH₃ O O 6-22 Cl F H CHF₂ CH₃ H H 6-23 Cl F H CHF₂ CH₃2,4-F₂- H benzoyl 6-24 Cl F H CHF₂ CH₃ 2-naphthoyl H

[0152] TABLE VII

No. X Y R R₁ R₂ R₃ R₄ R₅ 7-1 Cl F CH₃ CH₃ CF₃ Cl O O 7-2 Cl F CH₃ CH₃CF₃ Cl H H 7-3 Cl F H CH₃ CF₃ Cl H H 7-4 Cl F CH₃ CH₃ CF₃ Cl COCH₃ H 7-5Cl F CH₃ CH₃ CF₃ Cl benzoyl H 7-6 Cl Cl CH₃ CH₃ CF₃ Cl CH₃ CH₃ 7-7 Cl ClCH₃ CH₃ CF₃ Cl COOCH₃ H 7-8 Cl Cl CH₃ CH₃ CF₃ Cl CONHCH₃ H 7-9 CN F CH₃CH₃ CF₃ Cl benzoyl H 7-10 Cl H CH₃ CH₃ CF₃ Cl benzoyl H 7-11 Cl F CH₃CH₂CH₃ CF₃ Cl benzoyl H 7-12 Cl F CH₃ CH₃ OCHF₂ Cl benzoyl H 7-13 Cl FCH₃ CH₃ CF₃ Br benzoyl H 7-14 Cl F CH₃ CH₃ CF₃ Cl 2-naphthoyl H 7-15 ClF CH₃ CH₃ CF₃ Cl cinnamoyl H

[0153] TABLE VIII

No. X Y W R₄ R₅ 8-1 Cl F OH O O 8-2 Cl F OH H H 8-3 Cl F OCH_(2C≡CH) H H8-4 Cl F OCH(CH₃)₂ H H 8-5 Cl F O-c-pentyl H H 8-6 Cl F OCH₃ O O 8-7 ClF OCH₃ H H 8-8 Cl F OCH₃ 2,4-F₂-benzoyl H 8-9 Cl F OCH₃ 2-naphthoyl H8-10 Cl F OCH₃ 4-C₂H₅-benzoyl H 8-11 Cl F OCH₃ 3-phenyl-propionyl H 8-12CN F OCH₃ 2,4-F₂-benzoyl H 8-13 Cl F OCH₂C≡CH 2,4-F₂-benzoyl H 8-14 Cl FOCH₂C≡CH 2-naphthoyl H 8-15 Cl F OCH₂C≡CH 4-C₂H₅-benzoyl H 8-16 Cl FOCH₂C≡CH 3-phenyl-propionyl H 8-17 CN F OCH₂C≡CH 2,4-F₂-benzoyl H 8-18Cl F OCH(CH₃)₂ 2,4-F₂-benzoyl H 8-19 Cl F OCH(CH₃)₂ 2-naphthoyl H 8-20Cl F OCH(CH₃)₂ 4-C₂H₅-benzoyl H 8-21 Cl F OCH(CH₃)₂ 3-phenyl-propionyl H8-22 CN F OCH(CH₃)₂ 2,4-F₂-benzoyl H 8-23 Cl F OCH₃ COCH₃ H 8-24 Cl FOCH₃ benzoyl H 8-25 Cl F OCH₃ CH₃ CH₃ 8-26 Cl F OCH₃ COOCH₃ H 8-27 Cl FOCH₃ CONHCH₃ H 8-28 CN F OCH₃ benzoyl H 8-29 Cl H OCH₃ benzoyl H 8-30 ClF OCH₃ 4-vinyl-benzoyl H 8-31 Cl F OCH₃ cinnamoyl H 8-32 Cl NO₂ H O O8-33 Cl H H O O 8-34 NO₂ H H O O 8-35 Cl H H H H 8-36 Cl H H 2-naphthoylH

[0154] TABLE IX

No. X Y W R₄ R₅ R₈ R₉ 9-1 Cl F OH O O O O 9-2 Cl F OH H H O O 9-3 Cl FOCH₃ O O O O 9-4 Cl F OCH₃ H H O O 9-5 Cl F OCH₃ COCH₃ H O O 9-6 Cl FOCH₃ benzoyl H O O 9-7 Cl F OCH₃ CH₃ CH₃ O O 9-8 Cl F OCH₃ COOCH₃ H O O9-9 Cl F OCH₃ CONHCH₃ H O O 9-10 CN F OCH₃ benzoyl H O O 9-11 Cl H OCH₃benzoyl H O O 9-12 Cl H H O O O S 9-13 Cl H H H H O S 9-14 Cl H H2-naphthoyl H O S 9-15 Cl F OCH₃ 2-naphthoyl H O O 9-16 Cl F OCH₃2,4-F₂-benzoyl H O O 9-17 Cl H H O O O O 9-18 Cl H H H H O O 9-19 Cl H H2-naphthoyl H O O

[0155] TABLE X

No. X Y R R₅ R₄ 10-1 Cl F H O O 10-2 Cl F H H H 10-3 Cl F CH₃ O O 10-4Cl F CH₃ H H 10-5 Cl F CH₃ COCH₃ H 10-6 Cl F CH₃ benzoyl H 10-7 Cl F CH₃CH₃ CH₃ 10-8 Cl F CH₃ COOCH₃ H 10-9 Cl F CH₃ CONHCH₃ H 10-10 CN F CH₃benzoyl H 10-11 Cl H CH₃ benzoyl H

[0156] TABLE XI

No. X Y W R₁ R₂ Z 11-1 Cl F OCH₃ H CF₃ NO₂ 11-2 Cl F OH H CF₃ NO₂ 11-3Cl F OH H CF₃ NH₂ 11-4 Cl F OCH₃ H CF₃ NH₂ 11-5 Cl F OCH₃ H CF₃ NHCH₃11-6 Cl F OCH₃ H CF₃ NH-2-naphthoyl 11-7 Cl F OCH₃ H CF₃ Cl 11-8 Cl FOCH₃ H CF₃ CH₂CHClCOOCH₂CH₃ 11-9 Cl F OH CH₃ CF₃ NO₂ 11-10 Cl F OH CH₃CF₃ NH₂ 11-11 Cl F OCH₃ CH₃ CF₃ NH₂ 11-12 Cl F OCH₃ CH₃ CF₃ NHCH₃ 11-13Cl F OCH₃ CH₃ CF₃ NH-2-naphthoyl 11-14 Cl F OCH₃ CH₃ CF₃ NO₂ 11-15 Cl FOCH₃ CH₃ CF₃ NHCOCH₃ 11-16 Cl F OCH₃ CH₃ CF₃ NH-benzoyl 11-17 Cl F OCH₃CH₃ CF₃ N-(CH₃)₂ 11-18 Cl F OCH₃ CH₃ CF₃ NHCOO-phenyl 11-19 Cl F OCH₃CH₃ CF₃ NHCONHCH₃ 11-20 CN F OCH₃ CH₃ CF₃ 2-naphthoyl-NH 11-21 Cl F OCH₃CH₃ CH₃ 2-naphthoyl-NH 11-22 Cl H OCH₃ CH₃ CF₃ 2-naphthoyl-NH 11-23 Cl FOCH₃ CH₃ CF₃ Cl 11-24 Cl F OCH₃ CH₃ CF₃ CH₂CHClCOOCH₂CH₃

[0157] TABLE XII

No. X Y W R₄ R₅ R₈ R₉ 12-1 Cl F OH O O S O 12-2 Cl F OH H H S O 12-3 ClF OH H H S O 12-4 Cl F OCH₃ H H S O 12-5 Cl F OCH₃ 2-naphthoyl H S O12-6 Cl H H O O O O 12-7 Cl H H H H O O 12-8 Cl H H 2-naphthoyl H O O12-9 Cl F OCH₃ COCH₃ H S O 12-10 Cl F OCH₃ benzoyl H S O 12-11 Cl F OCH₃CH₃ CH₃ S O 12-12 Cl F OCH₃ COO-phenyl H S O 12-13 Cl F OCH₃ CONHCH₃ H SO 12-14 CN F OCH₃ 2-naphthoyl H S O 12-15 Cl H OCH₃ 2-naphthoyl H S O

[0158] TABLE XIII

No. X Y W R₄ R₅ 13-1 Cl F OH O 0 13-2 Cl F OH H H 13-3 Cl F OCH₃2-naphthoyl H 13-4 Cl F OCH₃ 2,4-difluorobenzoyl H 13-5 Cl H H2-naphthoyl H 13-6 Cl F OCH₃ COCH₃ H 13-7 Cl F OCH₃ benzoyl H 13-8 Cl FOCH₃ CH₃ CH₃ 13-9 Cl F OCH₃ COO-phenyl H 13-10 Cl F OCH₃ CONHCH₃ H 13-11CN F OCH₃ 2-naphthoyl H 13-12 Cl H OCH₃ 2-naphthoyl H

[0159] TABLE XIV

No. X Y W Q R₁ R₂ R₃ Z R₈ R₉ 14-1 Cl F OCH₃ Q1 CH₃ CF₃ H CH₂CH₂CO₂CH₂CH₃O O 14-2 Cl F OCH₃ Q1 CH₃ CF₃ H CH═CHCO₂CH₂CH₃ O O 14-3 Cl F OCH₃ Q1 CH₃CF₃ H CH₂CHClCO₂CH₃ O O 14-4 Cl F OCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂C₂H₅ O O(isomer-1) 14-5 Cl F OCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂C₂H₅ O O (isomer-2)14-6 Cl F OCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂-n-C₃H₇ O O (isomer-1) 14-7 Cl FOCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂-n-C₃H₇ O O (isomer-2) 14-8 Cl F OCH₃ Q1 CH₃CF₃ H CH₂CHClCO₂-n-C₄H₉ O O (isomer-1) 14-9 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-n-C₄H₉ O O (isomer-2) 14-10 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-n-C₅H₁₁ O O (isomer-1) 14-11 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-n-C₅H₁₁ O O (isomer-2) 14-12 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-n-C₆H₁₃ O O (isomer-1) 14-13 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-n-C₆H₁₃ O O (isomer-2) 14-14 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-i-C₄H₉ O O (isomer-1) 14-15 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-i-C₄H₉ O O (isomer-2) 14-16 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-i-C₅H₁₁ O O (isomer-1) 14-17 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-i-C₅H₁₁ O O (isomer-2) 14-18 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂-t-C₄H₉ O O 14-19 Cl F OCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂—CH₂C≡CH OO (isomer-1) 14-20 Cl F OCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂—CH₂C≡CH O O(isomer-2) 14-21 Cl F OCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂CH₂CF₃ O O 14-22 Cl FOCH₃ Q1 CH₃ CF₃ H CH₂CHClCO₂—CH₂CF₂CHF₂ O O 14-23 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CF₂CF₂CF₃ O O (isomer-1) 14-24 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CF₂CF₂CF₃ O O (isomer-2) 14-25 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CH₂OCH₃ O O 14-26 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CH₂OC₂H₅ O O 14-27 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CH₂OPh O O (isomer-1) 14-28 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CH₂OPh O O (isomer-2) 14-29 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂—CH₂CH₂CN O O 14-30 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CH₂BrCH₂Br O O (isomer-1) 14-31 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHClCO₂CH₂CH₂BrCH₂Br O O (isomer-2) 14-32 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHBrCO₂C₂H₅ (isomer-1) O O 14-33 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂CHBrCO₂C₂H₅ (isomer-2) O O 14-34 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂C₂H₅ O O 14-35 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂-n-C₃H₇ O O 14-36 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂-n-C₄H₉ O O 14-37 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂-n-C₅H₁₁ O O 14-38 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂-n-C₆H₁₃ O O 14-39 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂-i-C₃H₇ O O 14-40 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂-i-C₄H₉ O O 14-41 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH₂Ph O O 14-42 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH═CH₂ O O 14-43 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH₂CH═CH₂ O O 14-44 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH₂C≡CH O O 14-45 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH₂CF₂CHF₂ O O 14-46 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH(CF₃)₂ O O 14-47 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH₂CH₂OCH₃ O O 14-48 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂—CH₂CH₂SCH₃ O O 14-49 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₃)ClCO₂-tetrahydrofurfuryl O O 14-50 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CH₂CO₂CH₃)ClCO₂C₂H₅ O O 14-51 Cl F OCH₃ Q1 CH₃ CF₃ HCH₂C(CN)ClCO₂C₂H₅ O O 14-52 Cl F H Q5 CHF₂ CH₃ — CH₂CHClCO₂C₂H₅ — —14-53 Cl F OCH₃ Q6 — — — CH₂CHClCO₂C₂H₅ O O 14-54 Cl F CH₃ Q1 CH₃ CF₃ HCH₂CClCOOCH₂CH₃ O O 14-55 Cl F CH₃ Q1 CH₃ CF₃ H CH₂CClCOOCH₂CH₃ O O14-56 Cl F OCH₃ Q3 CH₃ CF₃ Cl CH₂CClCOOCH₂CH₃ — — 14-57 Cl H H Q1 CH₃CF₃ H CO-phenyl O O 14-58 Cl H H Q1 CH₃ CF₃ H (cis)CHCH-2-naphthyl O O14-59 Cl H H Q1 CH₃ CF₃ H (trans)CHCH-2-naphthyl O O 14-60 Cl F H Q1 CH₃CF₃ H CH₂(Cl)CHCOOCH₂CH₃ O O 14-61 Cl F OCH₃ Q5 CH₃ CF₃ HCH₂(Cl)CHCOOCH₂CH₃ O O 14-62 Cl F OCH₂CH₃ Q1 CH₃ CF₃ H Cl O O 14-63 Cl FOCH₂CH₃ Q1 CH₃ CF₃ H CH₂CHClCOOCH₂CH₃ O O 14-64 Cl F OCH₂CH₃ Q1 CH₃ CF₃H CH₂CHClCOOCH₂CH₃ O O 14-65 Cl F OCH₂CH₃ Q1 CH₃ CF₃ HCH₂CHClCOOCH₂CH₂CH₃ O O 14-66 Cl F OCH₂CH₃ Q1 CH₃ CF₃ HCH₂CHClCOOCH₂CH₂CH₃ O O 14-67 Cl F OCH(CH₃)₂ Q1 CH₃ CF₃ H Cl O O 14-68Cl F OCH(CH₃)₂ Q1 CH₃ CF₃ H CH₂CHClCOOCH₂CH₃ O O 14-69 Cl F OCH(CH₃)₂ Q1CH₃ CF₃ H CH₂CHClCOOCH₂CH₃ O O 14-70 CH₃ H H Q1 CH₃ CF₃ HCH₂CHClCOOCH₂CH₃ O O 14-71 COOCH₃ H H Q1 CH₃ CF₃ H CH₂CHClCOOCH₂CH₂CH₃ OO 14-72 Cl F OCH₃ Q8 CH₃ CF₃ H CH₂CHClCOOCH₂CH₂CH₃ O O 14-73 Cl F OCH₃Q1 CH₃ CF₃ H CH₂CHClCOOH O O 14-74 Cl F OCH₃ Q9 H CF₃ Cl NO₂ — — 14-75Cl F OCH₃ Q9 H CF₃ Cl NH₂ — — 14-76 Cl F OCH₃ Q9 H CF₃ Cl NH-2-naphthoyl— — 14-77 Cl F OCH₃ Q9 H CF₃ Cl CH₂CHClCOOCH₂CH₃ — —

[0160] TABLE XV

No. X Y W R₁ R₂ R₄ R₅ R₈ R₉ 15-1 Cl F OCH₃ CH₃ CF₃ NH₂ H O O 15-2 Cl FOCH₃ CH₃ CF₃ c-C₃H₅-carbonyl-NH— H O O 15-3 Cl F OCH₃ CH₃ CF₃benzoyl-NH— H O O 15-4 Cl F OCH₃ CH₃ CF₃ 2,4-F₂-benzoyl-NH— H O O 15-5Cl F OCH₃ CH₃ CF₃ 2-naphthoyl-NH— H O O 15-6 Cl F OCH₃ CH₃ CF₃ethoxycarbonyl-NH— H O O 15-7 Cl F OCH₃ CH₃ CF₃ phenoxycarbonyl-NH— H OO 15-8 Cl F OCH₃ CH₃ CF₃ 2,4-F₂-PhNHC(O)—NH— H O O 15-9 Cl F OCH₃ CH₃CF₃ H₅C₂OC(O)N(CH₃)C(O)—NH— H O O 15-10 Cl F OCH₃ CH₃ CF₃ H₂C═CHCH═N— HO O 15-11 Cl F OCH₃ CH₃ CF₃ c-C₃H₅—CH═N— H O O 15-12 Cl F OCH₃ CH₃ CF₃H₃CC(CH₃)═N— H O O 15-13 Cl F OCH₃ CH₃ CF₃ H₃COCH₂C(CH₃)═N— H O O 15-14Cl F OCH₃ CH₃ CF₃ H₃CS CH₂CH₂CH═N— H O O 15-15 Cl F OCH₃ CH₃ CF₃PhCH₂CH═N— H O O 15-16 Cl F OCH₃ CH₃ CF₃ H₅C₂OC(O)CH₂C(CH₃)═N— H O O15-17 Cl F OCH₃ CH₃ CF₃ PhCH(CH₃)CH═N— H O O 15-18 Cl F OCH₃ CH₃ CF₃

H O O 15-19 Cl F OCH₃ CH₃ CF₃

H O O 15-20 Cl F OCH₃ CH₃ CF₃ 2,4-F₂—PhCH═N— H O O 15-21 Cl F OCH₃ CH₃CF₃ F₃CC(CF₃)═N— H O O 15-22 Cl F OCH₃ CH₃ CF₃ 2-naphthyl-CH═N— H O O

[0161] TABLE XVI

No. X Y W R₁ R₂ R₄ R₈ R₉ 16-1 Cl Cl H CH₃ CF₃ H O O 16-2 Cl Cl H CH₃ CF₃CH₃ O O 16-3 Cl Cl H CH₃ CF₃ 2,4-F₂-benzyl O O 16-4 Cl Cl H CH₃ CF₃2,4-F₂-benzoyl O O 16-5 Cl Cl H CH₃ CF₃ 2-naphthoyl O O 16-6 Cl F OCH₃CH₃ CF₃ H O O 16-7 Cl F OCH₃ CH₃ CF₃ 2-naphthoyl O O 16-8 Cl F OCH₃ CH₃CF₃ CH₂-2-naphthyl O O 16-9 Cl F OCH₃ CH₃ CF₃ 2-naphthoyl O S 16-10 Cl FOCH₃ CH₃ CF₃ 2-naphthoyl S O 16-11 CN F OCH₃ CH₃ CF₃ 2-naphthoyl O O16-12 Cl H OCH₃ CH₃ CF₃ 2-naphthoyl O O 16-13 Cl F OCH₃ CH₃ CF₃CONH-phenyl O O 16-14 Cl F OCH₃ CH₃ CF₃ CONHCH₃ O O

[0162] TABLE XVII

No. X Y W R₁ R₂ R₄ R₈ R₉ 17-1 Cl F OCH₃ CH₃ CF₃ methyl O O 17-2 Cl FOCH₃ CH₃ CF₃ isopropyl O O 17-3 Cl F OCH₃ CH₃ CF₃ benzyl O O 17-4 Cl FOCH₃ CH₃ CF₃ 2-naphthyl O O 17-5 Cl F OCH₃ CH₃ CF₃ 2-hydroxyethyl O O17-6 Cl F OCH₃ CH₃ CF₃ benzyl O S 17-7 Cl F OCH₃ CH₃ CF₃ benzyl S O 17-8CN F OCH₃ CH₃ CF₃ benzyl O O 17-9 Cl H OCH₃ CH₃ CF₃ benzyl O O 17-10 ClF OCH₂CH₃ CH₃ CF₃ benzyl O O

[0163] TABLE XVIII ¹H NMR data No. NMR (CDCl₃, 300 Mhz) ppm 1-1(CDCl₃+CD₃OD) 4.04 (3H, s), 6.19 (1H, s), 7.57 (1H, d, J=8.6 Hz) 1-2(DMSO-d₆), 3.30 (2H, br s), 6.54 (1H, s), 8.12 (1H, d, J=9.2 Hz) 1-3(CDCl₃+CD₃OD) 3.85 (3H, s), 6.2 (1H, s), 6.58 (1H, d, J=9.4 Hz) 1-4 3.57(3H, br q, J=1.2 Hz), 3.86 (3H, s), 4.04 (2H, br s), 6.37 (1H, s), 6.66(1H, d, J=9.4 Hz) 1-5 3.55 (3H, hr g, J=1.1 Hz), 4.04 (3H, s), 6.33 (1H,s), 7.51 (1H, d, J=8.6 Hz) 1-6 3.57 (3H, g, J=1.1 Hz), 6.38 (1H, s),7.85 (1H, d, J=8.0 Hz), 10.57 (1H, br) 1-7 3.52 (3H, g, fr=0.7 Hz), 3.82(3H, s), 4.13 (2H, br), 6.32 (1H, s), 6.79 (1H, d, ~k9.1 Hz) 1-8 3.48(3H, s), 4.90 (3H, br), 6.30 (1H, s), 6.69 (1H, d, J=9.0 Hz) 1-9(Acetone-d₆) 3.68 (3H, br g, J=1.4 Hz), 4.05 (3H, s), 8.03 (1H, d, J=9.1Hz) 1-10 3.52 (3H, br s), 3.86 (3H, s), 4.05 (2H, br s), 4.63 (2H, brs), 6.66 (1H, d, J=9.7 Hz) 1-11 2.74 (6H, s), 3.57 (3H, br s), 3.84 (3H,s), 6.35 (1H, s), 7.01 (1H, d, J=8.8 Hz) 1-12 4.05 (3H, s), 4.61 (2H,s), 6.24 (1H, s), 7.52 (1H, d, J=8.6 Hz) 1-13 3.78 (3H, s), 5.24 (2H,s), 5.41 (2H, br s), 6.21 (1H, s), 6.56 (1H, d, J=9.5 Hz) 1-14 1.43 (3H,m), 4.06 (3H, s), 4.31 (2H, m), 6.32 (1H, s), 7.56 (1H, m) 1-15 1.15(3H, m), 3.85 (3H, s), 3.35 (2H, m), 6.48 (1H, s), 6.55 (1H, m) 1-16(CDCl₃+CD₃OD) 3.55 (3H, br g, J=1.1 Hz), 6.36 (1H, s), 6.61 (1H, d,J=9.2) 1-17 3.57 (3H, d, J=1.2 Hz), 6.38 (1H, s), 7.67 (1H, d, J=8.3Hz), 10.47 (1H, br s) 1-18 3.51 (3H, hr q, J=0.9 Hz), 4.94 (2H, s), 5.66(2H, br s), 6.39 (1H, s), 6.65 (111 d, J=9.4 Hz) 1-19 2.58 (1H, m), 3.55(3H, hr q, J=4.3 Hz), 4.17 (2H, br s), 4.7 (2H, d, J=2.4 Hz), 6.35 (1H,s), 6.65 (1H, d, J=9.3 Hz) 1-20 3.57 (3H, d, J=0.8 Hz), 3.78 (3H, s),4.02 (2H, br s), 4.65 (2H, dd, J=4.4, 1.9 Hz), 6.28 (1H, dt, J=15.7, 1.9Hz), 6.65 (1H, d, J=9.3 Hz), 7.01 (1H, dt, J=15.7, 4.4 Hz) 1-211.63-1.94 (8H, m), 3.55 (3H, s), 3.97 (2H, s), 4.8 (1H, m), 6.34 (1H,s), 6.65 (1H, d, J=9.6 Hz) 1-22 3.54 (3H, br q, J=~1.1 Hz), 3.94 (2H, brs), 5.0 (2H, s), 6.34 (1H, s), 6.69 (1H, d, Jr=9~4 Hz), 7.3-7.5 (5H, m)1-23 3.58 (3H, br q, J=1.2 Hz), 4.15 (2H, br s), 6.38 (1H, s), 6.78 (1H,d, J=9.2 Hz), 7.22 (1H, m), 8.36 (2H, m) 1-30 3.52 (3H, hr g, J=1.1 Hz),3.75 (3H, s), 6.31 (1H, s), 7.22 (1H, d, ~k8.8 Hz) 1-31 2.87 (3H, s),2.96 (3H s), 3.53 (3H, s), 3.64 (3H, s), 6.30 (1H, s), 6.86 (1H, d,J=8.9 Hz), 7.68 (1H, s) 1-32 1.83 (4H, m), 3.21 (4H, m), 3.55 (3H, brs), 3.72 (3H, s), 6.34 (1H, s), 6.86 (1H, d, J=8.9 Hz) 1-33 1.27 (3H, t,J=7.1 Hz), 4.20 (2H, g, J=7.1 Hz), 6.21 (1H, s), 7.62 (1H, d, J=8.8 Hz)1-34 1.26 (3H, t, J=7.1 Hz), 4.16 (2H, q, J=7.1 Hz), 3.53 (3H, s), 6.35(1H, s), 7.70 (1H, d, J=8.5 Hz) 1-36 2.40 (3H, d, J=1.1 Hz), 3.54 (3H,d, J=1.3 Hz), 6.33 (1H, s), 7.51 (1H, d, J=8.5 Hz) 1-37 2.23 (3H, d,J=0.9 Hz), 3.57 (3H, d, J1.1 Hz), 6.38 (1H, s), 6.74 (1H, d, J=9.4 Hz)1-38 3.57 (3H, d, J=1.1 Hz), 4.17 (2H, br s), 6.37 (1H, s), 6.50 (1H, t,1k74.0 Hz), 6.72 (1H, d, J=9.1 Hz) 1-40 3.56 (3H, d, J=1.1 Hz), 3.96(3H, s), 6.36 (1H, s), 7.07 (1H, d, J=8.7 Hz) 1.8 Hz), 8.54 (1H, d,J=1.8FIz) 1-44 3.57 (3H, d, J=1.1 Hz), 6.39 (1H, s), 7.13 (3H, m) 1-453.58 (3H, d, J=1.2 Hz), 6.38 (1H, s), 7.87 (1H, s), 10.61 (1H, br s)1-46 3.55 (3H, d, J=1.2 Hz), 3.93 (3H, s), 6.37 (1H, s), 7.27 (2H, m),7.77 (1H, dd, J=2.1, 1.0 Hz) 1-47 3.50 (3H, d, J=0.9 Hz), 3.81 (3H, s),3.96 (2H, s), 6.31 (1H, s), 6.88 (1H, s) 1-48 1.27 (3H, t, J=7.1 Hz),1.58 (3H, d, J=6.8 Hz), 3.55 (3H, d, J=1.1 Hz), 3.64 (2H, br s), 4.22(2H, m), 4.70 (1H, q, J=6.8 Hz), 6.36 (1H, s), 6.38 (2H, m), 6.88 (1H,d, J=9.2 Hz) 1-49 1.29 (3H, t, J=7.1 Hz), 1.68 (3H, d, J=6.8 Hz), 3.54(3H, d, J=1.0 Hz), 4.26 (2H, m), 4.82 (1H, g, J=6.8 Hz), 6.36 (1H, s),7.25 (2H, m), 7.74 (1H, m) 1-50 3.57 (3H, q, J=1.2 Hz), 6.38 (1H, s),6.65 (1H, t, J=71.1 Hz), 7.37 (1H, dd, J=9.3, 2.7 Hz , 7.85 1H, dd,J=2.7, 2.5 Hz 1-51 3.49 (3H, d, J=1.0 Hz), 6.30 (3H, m), 6.42 (1H, t,J=73.2 Hz), 7.8 (2H, br s) 1-52 3.57 (3H, d, J=1.2 Hz), 6.40 (1H, s),7.57 (1H, d, J=8.2 Hz), 8.04 (1H, dd, J=8.2, 1.6 Hz), 8.53 (1H, m) 1-531.27 (1.5H, t, J=7.1 Hz), 1.28 (1.5H, t, J=7.1 Hz), 1.44 (1.5H, d, J=6.9Hz), 1.45 (1.5H, d, J=6.9 Hz), 3.58 (3H, s), 4.08 (1H, m), 4.20 (2H, q,J=7.1 Hz), 4.39 (0.5H, d, J=7.2 Hz), 4.43 (0.5H, d, J=7.2 Hz), 6.26 (1H,m), 6.39 (2H, m), 6.50 (1H, t, J=73.3 Hz) 1-54 1.27 (1.5H, t, J=7.1 Hz),1.28 (1.5H, t, J=7.1 Hz), 1.44 (1.5H, d, J=6.9 Hz), 1.46 (1.5H, d, J=6.9Hz), 3.57 (3H, m), 4.11 (1H, m), 4.22 (2H, m), 4.35 (0.5H, d, J=7.4 Hz),4.43 (0.5H, d, J=7.1 Hz), 6.36 (0.5H, s), 6.38 (0.5H, s), 6.49 (1H, m),6.62 (1H, dd, J=9.1, 2.0 Hz) 1-55 1.22 (1.5H, t, J=7.1 Hz), 1.23 (1.5H,t, J=7.1 Hz), 1.36 (1.5H, d, J=6.9 Hz), 1.38 (1.5H, d, J=6.9 Hz), 3.55(3H, m), 3.82 (1.5H, s), 3.86 (1.5H, s), 4.0-4.4 (4H, m), 6.36 (1H, s),6.76 (0.5H, d, J=9.1 Hz), 6.79 (0.5H, d, J=9.1 Hz) 1-56 4.73 (2H, br s),5.50 (3H, br), 6.16 (1H, s), 6.53 (1H, d, J=9.3 Hz) 1-57 4.42 (2H, brs), 4.70 (2H, br s), 4.72 (2H, s), 6.16 (1H, s), 6.60 (1H, d, J=9.1 Hz)1-58 3.77 (3H, s), 4.64 (2H, br s), 4.87 (2H, s), 5.28 (2H, br s), 6.17(1H, s), 6.52 (1H, d, J=9.2 Hz) 1-59 1.29 (3H, t, J=7.1 Hz), 3.55 (3H,q, J=1.0 Hz), 4.23 (2H, q, J=7.1 Hz), 4.64 (2H, s), 4.82 (2H, br s),6.35 (1H, s), 6.60 (1H, d, J=9.2 Hz) 1-60 1.27 (3H, t, J=7.1 Hz), 1.659(1.5H, d, J=7.0 Hz), 1.666 (1.5H, d, J=7.0 Hz), 3.55 (3H, s), 4.20 (2H,q, J=7.1 Hz), 4.73 (1H, m), 6.346 (0.5H, s), 6.355 (0.5H, s), 6.61 (1H,d, J=9.3 Hz) 1-61 1.41 (3H, t, J=7.0 Hz), 3.52 (3H, q, J=1.0 Hz), 4.04(2H, q, J=7.0 Hz), 4.10 (2H, br s), 6.32 (1H, s), 6.62 (1H, d, J=9.5 Hz)1-62 1.16 (3H, t, J=7.1 Hz), 1.42 (3H, t, J=7.1 Hz), 2.99 (2H, qJ=7.1Hz), 3.57 (3H, q, J=1.1 Hz), 4.03 (2H, q, J=7.1 Hz), 4.14 (1H, br s),6.35 (1H, s), 6.63 (1H, d, J=9.4 Hz) 1-63 1.35 (6H, d, J=6.2 Hz), 3.55(3H, q, J=1.2 Hz), 3.95 (2H, br s), 4.50 (1H, q, J=6.2 Hz), 6.34 (1H,s), 6.66 (1H, d, J=9.4 Hz) 1-64 1.06 (3H, t, J=6.3 Hz), 1.37 (6H, d,J=6.2 Hz), 3.57 (3H, q, J=1.2 Hz), 3.83 (2H, br s), 4.52 (1H, g, J=6.2Hz), 6.35 (1H, s), 6.70 (1H, d, J=9.3 Hz) 1-65 7.62 (1H, d, J=8.5 Hz),8.37 (1H, 2d, J=2.6 Hz, 8.4 Hz), 8.83 (1H, d, J=2.6 Hz) 1-66 3.56 (3H,s), 6.37 (1H, s), 6.86 (1H, d, J=~8.4 Hz), 7.77 (1H, d, J=8.4 Hz), 10.75(1H, broad) 1-67 3.56 (3H, s), 6.37 (1H, s), 8.55 (1H, s) 1-68 3.56 (3H,s), 6.39 (1H, s), 7.45 (111., d, J=8 .7 Hz), 7.64 ( 1H, 2d, J=1.7 Hz,8.7 Hz), 8.13 (1H, d, J=1.7 Hz) 1-69 4.15 (3H, s), 6.14 (1H, s), 8.51(1H, s), 12.8 (1H, broad) 1-70 6.26 (1H, s), 7.62 (1H, 2d, J=6.1 Hz, 8.3Hz), 8.3 (1H, broad) 1-71 3.56 (3H, s), 4.8 (3H, broad), 6.38 (1H, s),6.59 (1H, d, J=8.7 Hz), 6.85 (1H, d, J8.7 Hz) 1-72 3.56 (3H, s), 3.89(3H, s), 6.37 (1H, s), 6.75 (1H, d, J=8.7 Hz), 6.87 (1H, d, J8.7 Hz)1-73 3.55 (3H, s), 3.75 (2H, s), 6.36 (1H, s), 6.73 (2H, m), 7.01 (1H,2d, J=2.4 Hz, 6.9 Hz) 2-1 2.04 (3H, s), 3.57 (3H, br q, J=1.1 Hz), 3.86(3H, s), 6.30 (1H, s), 7.22 (1H, d, J=9.6 Hz) 2-2 2.29 (3H, s), 2.33(3H, s), 3.53 (3H, br s), 3.78 (3H, s), 6.3 (1H, s), 7.42 (1H, d, J=8.8Hz) 2-3 1.14 (9H, s), 3.56 (3H, s), 3.82 (3H, s), 6.29 (1H, s), 7.19(1H, d, J=9.0 Hz), 7.61 (1H, br s) 2-4 3.49 (3H, br q, J=1.0 Hz), 3.75(3H, s), 5.70-5.79 (2H, m), 6.26 (1H, s), 6.40-6.55 (4H, m), 7.42 (1H,d, J=8.7 Hz) 2-5 1.95 (3H, s), 3.55 (3H, br s), 3.84 (3H, s), 5.45 (1H,s), 5.70 (1H, s), 6.27 (1H, s), 7.20 (1H, d, J=9.0 Hz), 7.62 (1H, br s)2-6 1.90 (3H, s), 1.91 (3H, s), 3.49 (3H, br s), 3.79 (3H, s), 5.46 (2H,s), 5.64 (1H, s), 5.66 (1H, s), 6.27 (1H, s), 7.30 (1H, d, J=8.8 Hz) 2-71.86 (3H, s), 2.05 (3H, s), 3.56 (3H, br s), 3.82 (3H, s), 5.66 (1H, brs), 6.27 (1H, s), 7.17 (1H, d, J=9.0 Hz), 7.23 (1H, br s) 2-8 1.85 (6H,m), 2.12 (6H, m), 3.47 (3H, br q, J=1.0 Hz), 3.77 (3H, s), 5.91 (1H, m),5.98 (1H, m), 6.25 (1H, s), 7.34 (1H, d, J=8.7 Hz) 2-9 (CDCl₃+CD₃OD)3.86 (3H, s), 6.16 (1H, s), 7.37 (1H, d, J=8.9 Hz) 2-10 3.54 (3H, br s),3.86 (3H, s), 6.31 (1H, s), 7.32 (1H, d, J=9.0 Hz) 2-11 (CDCl₃+CD₃OD)3.55 (3H, br s), 4.87 (2H, s), 6.35 (1H, s), 7.44 (1H, d, J=8.7 Hz) 2-12(CDCL3+CD₃OD) 3.59 (3H, br s), 3.87 (3H, s), 7.37 (1H, d, J=8.8 Hz) 2-133.56 (3H, br g, J=1.1 Hz), 3.89 (3H, s), 4.08 (2H, s), 6.3 (1H, s), 7.25(1H, d, J=9 Hz) 2-14 3.52 (3H, brq, J=1.1 Hz), 3.74 (2H, m), 3.85 (3H,s), 6.39 (1H, s), 7.53 (1H, d, J=9.3 Hz), 9.03 (1H, m) 2-15 3.56 (3H,s), 3.91 (3H, s), 3.95 (3H, s), 6.29 (1H, s), 7.24 (1H, d, J=9.0 Hz),9.00 (1H, s) 2-16 1.27 (3H, t, J=7.1 Hz), 1.28 (3H, t, J=7.1 Hz), 3.42(2H, s), 3.57 (3H, br s), 4.04 (2H, s), 4.10-4.30 (4H, m), 6.40 (1H, s),7.33 (1H, d, J=9.8 Hz), 8.07 (1H, s) 2-17 0.95 (2H, m), 1.10 (2H, m),1.50 (1H, m), 3.55 (3H, s), 6.37 (1H, s), 7.22 (1H, d, J=9.0 Hz), 7.92(1H, br s), 8.41 (1H, br, s) 2-18 0.70-1.20 (8H, m), 1.96 (1H, m), 2.15(1H, m), 3.54 (3H, br s), 3.75 (3H, s), 6.35 (111 s), 7.38 (1H, d, J=8.6Hz) 2-19 1.40 (5H, m), 1.70 (5H, m), 2.25 (1H, m), 3.32 (3H, s), 3.82(3H, s), 6.34 (1H, s), 7.17 (1H, d, J=9.0 Hz), 7.68 (3H, s) 2-20 1.20(10H, m), 1.70 (10H, m), 2.50 (2H, m), 3.50 (3H, s), 3.68 (3H, s), 6.31(1H, s), 7.36 (1H, m) 2-21 3.37 (3H, s), 3.44 (3H, s), 3.55 (3H, br s),4.18 (3H, s), 6.33 (1H, s), 7.43 (1H, d, J=8.8 Hz) 3.2 (3H, s), 3.55(3H, s), 3.96 (3H, s), 6.35 (1H, s), 6.48 (1H, br s), 7.29 (1H, d, J=8.8Hz) 2-22 3.52 (3H, br s), 3.64 (3H, s), 6.29 (1H, s), 6.85 (1H, d, J=9.1Hz), 7.4 (5H, m), 7.68 (1H, s) 2-23 2.39 (3H, s), 3.52 (3H, s), 3.82(3H, s) 6.23 (f H, s), 7.20 (1H, d, J=9.0 Hz), 7.32 (2H, m), 7.53 (2H,m), 8.02 (lH, s) 2-24 2.42 (3H, s), 3.53 (3H, s), 3.82 (3H, s), 6.22(1H, s), 7.20 (1H, d, J=9.0 Hz), 7.26 (2H, d, J=7.8 Hz), 7.67 (2H, d,J=7.8 Hz), 7.91 (1H, s) 2-25 2.32 (3Hx2, s), 3.28 (3H, s), 3.82 (3H, s),6.02 (1H, s), 7.10 (4H, d, J=7.9 Hz), 7.26 (1H, d, 19.0 Hz), 7.73 (4H,m) 2-26 2.40 (3H, s), 3.44 (3H, s), 3.54 (3H, d, J=1.l Hz), 6.29 (1H,s), 6.55 (1H, br s), 7.18 (1H, d, J=8.9 Hz), 7.25 (2H, d, J=8.3 Hz),7.68 (2H, d, J=83 Hz) 2-27 1.26 (3H, t, J=7.7 Hz), 2.71 (2H, q, J=7.7Hz), 3.54 (3H, s), 3.83 (3H, s), 6.23 (1H, s), 7.21 (1H, d, J=9.0 Hz),7.29 (2H, d, J=8.2 Hz), 7.70 (2H, d, J=8.2 Hz), 7.86 (1H, br s) 2-281.26 (3H, t, J=7.6 Hz), 2.71 (2H, q, J=7.6 Hz), 3.51 (3H, br s), 4.78(2H, s), 6.25 (1H, s), 7.28 (3H, m), 7.73 (2H, m), 7.84 (1H, br s) 2-290.95 (6H, t, J=7.2 Hz), 1.66 (4H, m), 2.64 (4H, m), 3.53 (3H, br s),3.83 (3H, s), 6.23 (1H, s), 7.21 (1H, d, J=9.3 Hz), 7.27 (4H, m), 7.70(2H, m), 8.00 (2H, m) 2-30 1.35 (9H, s), 3.55 (3H, s), 3.83 (3H, s),6.23 (1H, s), 7.20 (1H, m), 7.49 (2H, d, J==8.6 Hz), 7.73 (2H, d, J=8.6Hz), 7.88 (1H, br s) 2-31 3.54 (3H, s), 3.83 (3H, s), 5.40 (1H, d,J=10.9 Hz), 5.87 (1H, d, J47.6 Hz), 6.78 (1H, dd, J=17.6, 10.9 Hz), 7.22(1H, d, J=9.0 Hz), 7.49 (2H, d, J=8.2 Hz), 7.75 (1H, d, J=8.2 Hz), 8.01(1H,brs) 2-32 2.31 (3H, s), 2.32 (3H, s), 3.54 (3H, d, J=1.0 Hz), 3.82(3H, s), 6.23 (1H, s), 7.19 (1H, d, J=9.1 Hz), 7.22 (1H, d, J=7.8 Hz),7.50 (1H, dd, J=7.8, 1.7 Hz), 7.56 (1H, br s), 7.86 (1H, br s) 2-33 3.62(3H, s), 3.84 (3H, s), 6.25 (1H, s), 7.25 (1H, d, J=8.9 Hz), 7.75 (2H,d, J8.3 Hz), 7.89 (2H, d, J=8.3 Hz), 7.92 (1H, br s) 2-34 3.54 (3H, brs), 3.84 (3H, s), 6.26 (1H, s), 7.30 (1H, d, J9.3 Hz), 7.72 (4H, m),7.94 (2H, m), 8.17 (2H, m) 2-36 3.56 (3H, d, J=1.1 Hz), 3.85 (3H, s),4.64 (2H, s), 6.25 (1H, s), 7.24 (1H, d, J9.0 Hz), 7.52 (2H, d, J=8.3Hz), 7.79 (2H, d, J=8.3 Hz), 7.91 (1H, br s) 2-37 3.53 (3H, s), 3,83(3H, s), 6.25 (1H, s), 7.20 (1H, d, J=9.0 Hz), 7.45 (3H, m), 7.63 (4H,m), 7.84 (2H, d, J=8.2 Hz), 8.13 (1H, s) 2-38 3.32 (3H, s), 3.86 (3H,s), 6.08 (1H, s), 7.52 (iSH, m), 7.95 (4H, m) 2-39 3.56 (3H, br s), 3.89(3H, s), 6.27 (1H, s), 7.15-7.3 (2H, m), 7.24 (1H, d, J=9.1 Hz), 7.54(1H, m), 7.92 (1H, m), 8.43 (1H, hr d, J=13.8 Hz) 2-40 3.53 (3H, br s),3.83 (3H, s), 6.23 (1H, s), 7.12 (2H, m), 7.22 (1H, d, J=9.1 Hz), 7.79(2H, m), 7.97 (1H, br s) 2-41 3.57 (3H, hr q, J=1.1 Hz), 3.9 (3H, s),6.29 (1H, s), 7.2 (1H, m), 7.26 (1H, d, J=9.1 Hz), 7.36 (1H, m), 7.63(1H, m), 8.29 (1H, d, J=11.1 Hz) 2-42 3.56 (3H, br s), 3.89 (3H, s),6.27 (1H, s), 6.97 (2H, m), 7.25 (1H, d, J=9 Hz), 7.97 (1H, m), 8.37(1H, hr d, J=13.3 Hz) 2-43 3.44 (3H, br s), 3.96 (3H, s), 6.24 (1H, s),6.64 (2H, m), 6.86 (2H, m), 7.35 (1H, d, J=8.8 Hz), 7.78 (2H, m) 2-443.88 (3H, s), 6.26 (1H, s), 6.98 (2H, m), 7.23 (1H, d, J=9 Hz), 7.96(1H, m), 8.46 (1H, m) 2-45 3.43 (3H, hr q, J=1.3 Hz), 5.1 (2H, s), 6.36(1H, s), 6.9-7.15 (4H, m), 7.77 (1H, d, J=9.1 Hz), 7.7-7.9 (2H, m) 2-463.52 (3H, s), 3.91 (3H, s), 6.75-7.05 (2H, m), 6.95 (1H, s), 7.39 (1H,d, J=8.9 Hz), 8.03 (1H, m), 8.56 (1H, m) 2-47 3.55 (3H, br s), 3.91 (3H,s), 6.32 (1H, s), 6.93 (2H, m), 7.25 (1H, d, J=8.9 Hz), 7.39 (1H, m),8.03 (1H,hrs) 2-48 3.55 (3H, br q, J=1.0 Hz), 3.83 (3H, s),45.26 (1H,s), 7.24 (1H, d, 19.1 Hz), 7.25 (1H, m), 7.54 (1H, m), 7.65 (1H, m),8.05 (1H, br s) 2-49 3.39 (3H, br s), 3.77 (3H, s), 6.1 (1H, s),7.10-7.40 (2H, m), 7.34 (1H, d, J=8.8 Hz), 7.60-8.00 (4H, m) 2-50 3.54(3H, br s), 3.81 (3H, s), 6.26 (1H, s), 7.01 (1H, m), 7.25 (1H, d, J=9.3Hz), 7.31 (2H, m), 8.28 (1H, s) 2-51 3.43 (3H, br s), 3.79 (3H, s), 6.15(1H, s), 6.95-7.75 (7H, m) 2-53 3.56 (3H, d, J=1.2 Hz), 3.91 (3H, s),6.32 (1H, s), 7.26 (1H, d, J=9.0 Hz), 7.35 (1H, ddd, J=8.6, 6.1, 2.5Hz), 7.42 (2H, m), 7.52 (1H, dd, J=7.4, 1.2 Hz), 7.83 (1H, br s) 2-543.53 (3H, s), 3.82 (3H, s), 6.26 (1H, s), 7.22 (1H, d, J=9.0 Hz), 7.39(1H, dd, J=7.8, 7.9 Hz), 7.53 (1H, m), 7.62 (1H, m), 7.77 (1H, m), 8.06(1H, br s) 2-55 3.36 (3H, s), 3.81 (3H, s), 6.11 (1H, s), 7.30 (3H, m),7.43 (2H, m), 7.76 (4H, m) 2-56 3.53 (3H, s), 3.83 (3H, s), 6.23 (1H,s), 7.23 (1H, d, J=9.0 Hz), 7.44 (2H, d, J=8.7 Hz), 7.72 (2H, d, J=8.7Hz), 7.92 (1H, s) 2-57 3.32 (3H, s), 3.78 (3H, s), 6.06 (1H, s), 7.34(SH, m), 7.80 (4H, m) 2-58 3.56 (3H, d, J=1.0 Hz), 3.89 (3H, s), 6.32(1H, s), 7.27 (1H, d, J9.0 Hz), 7.31 (1H, dd, J=8.1, 1.9 Hz), 7.47 (2H,m), 7.92 (1H, br s) 2-59 3.55 (3H, d, J=1.1 Hz), 3.84 (3H, s), 6.25 (1H,s), 7.25 (1H, d, J=9.1 Hz), 7.54 (1H, d, J=8.3 Hz), 7.60 (1H, dd, J=8.3,2.0 Hz), 7.88 (1H, br s), 7.89 (1H, d, J=2.0 Hz) 2-60 3.54 (3H, br s),3.83 (3H, s), 6.26 (1H, s), 7.24 (1H, d, J=9.0 Hz), 7.34 (2H, m), 7.65-7.75 (2H, m), 7.92-8.25 (4H, m) 2-61 3.53 (3H, s), 3.82 (3H, s), 6.23(1H, s), 7.22 (1H, d, J=9.0 Hz), 7.61 (4H, m), 7.95 (1H, s) 2-62 3.33(3H, s), 3.80 (3H, s), 6.06 (1H, s), 7.31 (1H, d, J=9.0 Hz), 7.51 (4H,m), 7.73 (4H, m) 2-63 3.54 (3H, d, J=1.1 Hz), 3.83 (3H, s), 3.87 (3H,s), 6.22 (1H, s), 6.95 (2H,d, J=8.8 Hz), 7.21 (1H, d, J=9.1 Hz), 7.75(2H, d, J=8.8 Hz), 7.78 (1H, hr. s) 2-64 1.44 (3H, t, J=7.0 Hz), 3.52(3H, s), 3.82 (3H, s), 4.06 (2H, q, J=7.0 Hz), 6.22 (1H, s), 6.90 (2H,d, J=9.0 Hz), 7.20 (1H, d, J=9.0 Hz), 7.73 (2H, d, J9.0 Hz), 7.91 (1H,s) 2-66 3.55 (3H, d, J=1.0 Hz), 3.84 (3H, s), 6.25 (1H, s), 7.25 (1H, d,J=9.1 Hz), 7.51 (2H, d, J=8.6 Hz), 7.85 (2H, d, J=8.6 Hz), 7.88 (1H, brs) 2-67 3.85 (3H, s), 6.22 (1H, s), 7.25 (1H, d, J=9.9 Hz), 7.76 (2H, d,J=8.4 Hz), 7.85 (2H, d, J=8.4 Hz), 7.96 (1H, br s) 2-69 3.40 (3H, br s),3.79 (3H, s), 6.12 (1H, s), 7.36 (1H, d, J=8.7 Hz), 8.06 (4H, m), 8.25(4H, m) 2-70 3.50 (3H, br s), 3.87 (3H, s), 6.32 (1H, s), 7.51 (1H, d,J=8.8 Hz), 9.07 (2H, m), 9.12 (1H, m), 9.91 (1H, br s) 2-71 3.33 (3H,s), 3.77 (3H, s), 7.20 (4H, m), 7.31 (1H, d, J=8.8 Hz), 7.92 (4H, m)2-72 3.54 (3H, s), 3.83 (3H, s), 6.24 (1H, s), 7.25 (3H, m), 7.82 (2H,m), 8.02 (1H, s) 2-73 3.54 (3H, br s), 3.83 (3H, s), 6.05 (2H, s), 6.23(1H, s), 6.85 (1H, d, J=7.8 Hz), 7.21 (1H, d, J=8.8 Hz), 7.25-7.34 (2H,m), 7.80 (1H, br s) 2-74 3.52 (3H, s), 3.84 (3H, s), 6.25 (1H, s), 7.24(1H, d, J=9.0 Hz), 7.50 (4H, m), 7.90 (3H, m), 8.20 (1H, br s) 2-75 3.64(3H, s), 3.85 (3H, s), 6.24 (1H, s), 7.24 (1H, d, J=9.0 Hz), 7.80 (7H,m), 8.32 (1H, s) 2-76 3.87 (3H, s), 6.1 (1H, s), 7.31 (1H, d, J=9.0 Hz),7.60 (2H, m), 7.80-8.05 (SH, m), 8.38 (1H, s) 2-77 3.83 (3H, s), 4.69(2H, s), 6.21 (1H, s), 7.35 (1H, d, J=8.9 Hz), 7.50-7.60 (3H, m),7.80-7.85 (4H, m), 8.07 (1H, s) 2-78 3.56 (3H, s), 3.86 (3H, s), 6.28(1H, s),1i49 (1H, d, J=15.6 Hz), 7.21 (1H, d, J=9.0 Hz), 7.39 (4H, m),7.50 (2H, m), 7.63 (1H, d, J15.6 Hz) 2-79 3.57 (3H, s), 3.86 (3H, s),6.28 (1H, s)~, 6.54 (1H, d, J=15.7 Hz), 6.84-6.94 (3H, m), 7.22 (1H, d,J=9.0 Hz), 7.36 (1H, br s), 7.48 (1H, q, J=7.7 Hz), 7.67 (1H, d, J15.7Hz) 2-80 2.41 (3H, s), 3.57 (3H, s), 3.86 (3H, s), 6.29 (1H, s), 6.40(1H, d, J=15.4 Hz), 7.19-7.32 (4H, m), 7.33 (1H, br s), 7.53 (1H, d,J=7.2 Hz), 7.93 (1H, d, J=15.4 Hz) 2-81 2.12 (3H, d, J=1.3 Hz), 3.57(3H, d, J=0.9 Hz), 3.88 (3H, s), 6.29 (1H, s), 7.20 (1H, d, J=9.1 Hz),7.36 (5H, m), 7.66 (1H, br s) 2-82 3.57 (3H, br s), 3.85 (3H, s), 6.29(1H, s), 6.48 (1H, d, J15.6 Hz), 7.16 (1H, d, J9.0 Hz), 7.28 (2H, m),7.40 (1H, dd, J=7.9, 1.6 Hz), 7.53 (1H, dd, J=7.4, 1.6 Hz), 7.67 (1H, brs), 7.98 (1H, d, J=15.6 Hz) 2-83 3.46 (3H, br s), 3.83 (3H, s), 6.24(1H, s), 6.80 (1H, d, J15.5 Hz), 6.91 (1H, d, J15.5 Hz), 7.30 (4H, m),7.39 (2H, m), 7.45 (1H, d, J=8.8 Hz), 7.56 (1H, dd, J=7.6, 1.8 Hz), 7.59(1H, dd, J=7.6, 1.8 Hz), 8.18 (1H, d, J=15.5 Hz), 8.20 (1H, d, J=15.5Hz) 2-84 3.56 (3H, br s), 3.84 (3H, s), 6.29 (1H, s), 6.45 (1H, d,J=15.6 Hz), 7.18 (1H, d, J=9.0 Hz), 7.54 (2H, d, J=8.6 Hz), 7.40 (2H, d,J=8.6 Hz), 7.55 (1H, d, J=15.6 Hz), 7.59 (1H, brs) 2-85 3.56 (3H, br s),3.84 (3H, s), 3.85 (3H, s), 6.28 (1H, s), 6.35 (1H, d, J=15.5 Hz), 6.89(2H, d, J=~8.7 Hz), 7.19 (1H, d, J=9.0 Hz), 7.35 (1H, br s), 7.45 (2H,d, J=8.7 Hz), 7.58 (1H, d, J=15.5 Hz) 2-86 2.60 (2H, q, J=7.7 Hz), 2.91(2H, t, J=7.7 Hz), 3.56 (3H, s), 3.69 (3H, s), 6.26 (1H, s), 7.1-7.3(6H, m) 2-87 2.66 (2H, m), 2.92 (2H, m), 3.55 (3H, s), 4.52 (2H, s),6.28 (1H, s), 7.1-7.4 (6H, m) 2-88 1.90 (2H, tt, J=7.5, 7.4 Hz), 2.29(2H, d, J=7.4 Hz), 2.61 (2H, t, J=~7.5 Hz), 3.52 (3H, d, J=0.7 Hz), 3.84(3H, s), 6.28 (1H, s), 7.13-7.32 (7H, m) 2-89 3.54 (3H, s), 3.82 (3H,s), 4.02 (2H, s), 4.55 (2H, s), 6.15 (1H, s), 7.16 (1H, d, J9.0 Hz), 7.4(5H, m), 8.5 5 (1H, s) 2-90 3.56 (3H, d, J=1.1 Hz), 3.87 (3H, s), 6.26(1H, s), 6.55 (1H, dd, J=3.6, 1.8 Hz), 7.17 (1H, dd, J=3.6, 0.5 Hz),7.22 (1H, d, J=9.1 Hz), 7.54 (1H, dd, J=1.8, 0.5 Hz), 8.18 (1H, brs)2-91 2.25 (3H, s), 3.46 (3H, s), 3.81 (3H, s), 6.25 (1H, s), 6.39 (1H,s), 7.18 (1H, d, J=9.0 Hz), 7.39 (1H, s), 8.30 (1H, s) 2-92 3.56 (3H, d,J=0.8 Hz), 3.85 (3H, s), 6.28 (1H, s), 6.39 (1H, d, J=15.2 Hz), 6.48(1H, dd, J=3.4, 1.8 Hz), 6.60 (1H, d, J=3.4 Hz), 7.19 (1H, d, J=9.0 Hz),7.34 (1H, br s), 7.40 (1H, d, J=15.2 Hz), 7.48 (1H, d, J=1.8 Hz) 2-933.45 (3H, s), 3.66 (3H, s), 3.80 (2H, s), 6.16 (1H, s), 7.00 (4H, m),7.55 (1H, br s) 2-94 2.46 (3H, s), 3.56 (3H, s), 3.88 (3H, s), 6.26 (1H,s), 6.94 (1H, m), 7.20 (1H, d, J=9.0 Hz), 7.36 (1H, m), 7.65 (1H, s)2-95 2.45 (3H, s), 3.47 (3H, s), 3.78 (3H, s), 6.17 (1H, s), 6.70 (1H,m), 7.13 (1H, d, J=9.0 Hz), 7.32 (1H, m), 7.63 (1H, s) 2-96 2.41 (6H,s), 3.26 (3H, s), 3.78 (3H, s), 5.97 (1H, s), 6.59 (2H, m), 7.24 (1H, d,J=9.0 Hz), 7.39 (2H, m) 2-97 3.31 (3H, s), 3.84 (3H, s), 6.03 (1H, s),7.05 (2H, m), 7.40 (2H, m), 7.70 (3H, m) 2-98 3.54 (3H, s), 3.84 (3H,s), 6.25 (1H, s), 7.25 (1H, d, J=9.7 Hz), 7.41 (1H, dd, J=7.7, 4.8 Hz),8.01 (1H, d, J=7.7 Hz), 8.32 (1H, br s), 8.78 (1H, br s), 9.01 (1H, brs) 2-100 3.42 (3H, q, J=1.0 Hz), 3.79 (3H, s), 6.12 (1H, s), 7.35 (1H,d, J=8.6 Hz), 7.56 (1H, d, J=8.0 Hz), 7.39 (1H, d, J=8.0 Hz), 8.15 (1H,dd, J=8.0, 2.2 Hz), 8.16 (1H, dd, J=8.0, 2.2 Hz), 8.77 (1H, d, J=2.2Hz), 8.91 (1H, d, J=2.2 Hz) 2-101 3.59 (3H, br q, J=1.2 Hz), 6.36 (1H,s), 6.99 (1H, dd, J=4.9, 8.3 Hz), 7.27 (1H, d, J8.7 Hz), 8.44 (1H, dd,J=1.7, 4.8 Hz), 8.6 (1H, dd, J=1.7, 8.3 Hz), 9.79 (1H, br s) 2-102(CDCl₃+CD₃OD) 3.54 (3H, br s), 6.33 (1H, s), 6.82 (1H, t, J=5.0 Hz), 7.2(1H, d, J=8.8 Hz), 8.38 (2H, d, J=5.0 Hz) 2-103 3.55 (3H, q, J=1.0 Hz),3.~9 (3H, s), 6.26 (1H, s), 7.22 (1H, d, J=9.1 Hz), 7.45 (3H, m), 7.83(3H, m), 7.99 (1H, br s) 2-104 3.58 (3H, s), 3.92 (3H, s), 6.26 (1H, s),7.20 (1H, d, J=9.0 Hz), 7.65 (1H, m), 7.85 (2H, m), 8.17 (2H, m), 8.33(1H, m), 10.05 (1H, s) 2-105 3.60 (3H, br s), 3.92 (3H, s), 6.27 (1H,s), 7.27 (1H, d, J9.0 Hz), 7.93 (2H, m), 8.20 (2H, m), 9.60 (1H, s),10.12 (1H, s) 2-106 3.56 (3H, q, J=0.7 Hz), 3.86 (3H, s), 6.27 (1H, s),6.95 (2H, m), 7.41 (1H, d, J=8.7 Hz), 7.95 (1H, m) 2-113 3.56 (3H, q,J=1.0 Hz), 3.86 (3H, s), 6.26 (1H, d, J=15.2 Hz), 6.28 (1H, s), 7.05(1H, dd, J5.0, 3.6 Hz), 7.20 (1H, d, J=9.0 Hz), 7.25 (1H, d, J=3.6 Hz),7.27 (1H, br s), 7.38 (1H, d, J5.0 Hz), 7.75 (1H, d, J=15.2 Hz) 2-1143.56 (3H, d, J=0.9 Hz), 6.40 (1H, s), 7.28 (1H, d, J=9.21 Hz), 7.50-7.65(2H, m), 7.70- 7.80 (1H, m), 7.80-8.0 (3H, m), 8.35 (1H, m), 8,63 (1H,br s) 2-115 3.54 (3H, d, J=0.9 Hz), 6.24 (1H, s), 6.51 (1H, t, J=73.1Hz), 7.32 (1H, d, J=8.8 Hz), 7.50-7.65 (2H, m), 7.70-7.82 (1H, m),7.85-7.95 (3H, m), 8.07 (1H, br s), 8.29 (1H, br s) 2-116 2.09 (3H, s),2.14 (3H, s), 3.50 (3H, d, J1.0 Hz), 3.79 (3H, s), 4.8-5.0 (4H, m), 6.29(1H, s), 7.47 (1H, d, J=8.9 Hz) 2-117 2.18 (3H, s), 3.56 (3H, d, J=1.1Hz), 3.86 (3H, s), 4,58 (2H, s), 6.30 (1H, s), 7.24 (1H, d, J=9.0 Hz)2-118 1.40 (3H, t, J=7.1 Hz), 3.56 (3H, d, J=1.0 Hz), 3.91 (3H, s), 4.39(2H, q, J7.1 Hz), 6.29 (1H, s), 7.25 (1H, d, J=9.1 Hz), 9.01 (1H, br s)2-119 3.54 3H, s , 3.72 3H, s , 4.56 2H, s , 6.24 1H, s , 6.85-7.40 6H,m , 8.50 1H, br s 2-120 3.45 (3H, s), 3.85 (3H, s), 4.8-5.15 (4H, m),6.27 (1H, s), 6.8-7.0 (6H, m), 7.20-730 (4H, m), 7.48 (1H, d, J=8.7 Hz)2-121 3.59 (3H, s), 3.93 (3H, s), 6.35 (1H, s), 7.26 (1H, d, J=9.0 Hz),7.40-7.70 (3H, m), 8.20 (2H, m), 8.97 (1H, br s) 2-122 2.33 (3H, s),3.49 (3H, d, J=0.9 Hz), 6.24 (1H, s), 7.34 (1H, d, J=9.1 Hz), 7.50-7.62(2H, m), 7.75-7.95 (5H, m), 8.31 (1H, br s) 2-123 2.28 (3H, s), 3.54(3H, s), 6.29 (1H, s), 6.59 (1H, d, J=15.5 Hz), 7.20-7.50 (6H, m), 7.63(1H, d, J=15.5 Hz) 2-124 2.29 (6H, s), 3.56 (3H, s), 3.93 (3H, s), 6.32(1H, s), 7.05 (2H, m), 7.20 (2H, m), 7.47 (1H, br s) 2-125 3.57 (3H, s),3.87 (3H, s), 6.29 (1H, s), 6.62 (1H, d, J=15.7 Hz), 7.1-7.5 (5H, m),7.72 (1H, d, J=15.7 Hz) 2-126 3.52 (3H, s), 3.80 (3H, s), 6.24 (1H, s),6.32 (1H, d, J=15.6 Hz), 7.11 (1H, br d, J=8.8 Hz), 7.4-7.6 (4H, m),7.95 (2H, m) 2-127 3.56 (3H, s), 3.86 (3H, s), 3.89 (3H, s), 6.28 (1H,s), 6.64 (1H, d, J15.7 Hz), 6.95 (2H, m), 7.19 (1H, d, J=9.0 Hz), 7.35(2H, m), 7.46 (1H, dd, J7.6, 1.4 Hz), 7.88 (1H, d, J=15.7 Hz) 2-128 3.59(3H, s), 3.88 (3H, s), 6.31 (1H, s), 6.65 (1H, d, J=15.9 Hz), 7.20 (2H,m), 7.35 (2H, d, J=8.l Hz), 7.37 (1H, br s), 7.72 (1H, d, J=45.9 Hz)2-129 2.28 (3H, s), 2.53 (2H, t, J=7.3 Hz), 2.88 (2H, t, J=7.3 Hz), 3.56(3H, s), 3.73 (3H, s), 6.26 (1H, s), 7.11 (SH, m), 7.35 (1H, br s) 2-1302.33 (3H, s), 2.36 (3H, s), 3.57 (3H, s), 3.86 (3H, s), 6.29 (1H, s),6.40 (1H, d, J=15.4 Hz), 7.09 (2H, br s), 7.20 (1H, d, J=9.0 Hz), 7.33(1H, br s), 7.35 (1H, s), 7.90 (1H, d, J=15.4 Hz) 2-131 3.54 (3H, d,J=1.0 Hz), 6.37 (1H, s), 7.21 (1H, d, J=8.6 Hz), 7.33 (1H, dd, J=8.6,2.1 Hz), 7.60 (2H, m), 7.77 (1H, dd, J=8.6, 1.8 Hz), 7.88 (3H, m), 7.98(1H, br s), 8.01 (1H, d, J=2.l Hz), 8.26 (1H, d, J=1.3 Hz) 2-132 2.21(3H, s), 2.27 (3H, s), 2.48 (2H, t, J=7.8 Hz), 2.81 (2H, t, J=7.8 Hz),3.57 (3H, s), 3.73 (3H, s), 6.27 (1H, s), 6.92 (2H, m), 7.02 (1H, d,J=7.6 Hz), 7.12 (1H, br d, J=8.6 Hz), 7.51 (1H, br s) 2-133 3.55 (3H, d,J=1.0 Hz), 3.76 (3H, s), 4.52 (2H, s), 6.26 (1H, s), 6.88 (2H, dd,J=9.1, 2.4 Hz), 7.02 (2H, dd, J=9.1, 8.1 Hz), 7.20 (1H, d, J=9.0 Hz),8.48 (1H, br s) 2-134 3.57 (3H, s), 3.86 (3H, s), 6.28 (1H, s), 6.50(1H, d, J=15.5 Hz), 7.23 (1H, d, J=9.0 Hz), 7.35 (4H, m), 7.50 (1H, brs), 7.58 (1H, d, J=15.5 Hz) 2-135 3.55 (3H, d, J=1.0 Hz), 3.76 (3H, s),4.52 (2H, s), 6.26 (1H, s), 6.87 (2H, d, J=9.0 Hz), 7.20 (1H, d, J=9.0Hz), 7.29 (2H, d, J=9.0 Hz), 8.45 (1H, br s) 2-136 3.58 (3H, d, J=1.0Hz), 3.93 (3H, s), 6.33 (1H, s), 7.26 (1H, d, J=9.1 Hz), 7.54 (3H, m),7.95 (2H, d, J=8.3 Hz), 8.14 (1H, s), 8.28 (1H, s) 2-137 3.55 (3H, s),6.37 (1H, s), 6.40 (1H, d, J=15.5 Hz), 7.16 (1H, d, J=8.6 Hz), 7.19 (1H,br s), 7.29 (1H, dd, J=8.5, 1.9 Hz), 7.38 (3H, m), 7.48 (2H, m), 7.70(1H, d, J=15.5 Hz), 7.99 (1H, br s) 2-139 3.19 (3H, s), 5.98 (1H, s),7.17 (1H, dd, J=8.0, 1.2 Hz), 7.2-7.6 (7H, m), 7.7-7.9 (6H, m), 7.93(2H, dd, J=8.6, 1.7 Hz), 8.53 (2H, br s) 2-140 3.56 (3H, d, J=1.0 Hz),6.40 (1H, s), 7.42 (1H, d, J=8.3 Hz), 7.60 (3H, m), 7.78 (1H, dd, J=8.6,1.8 Hz), 7.92 (3H, m), 8.01 (1H, br s), 8.29 (1H, br s), 8.38 (1H, d,J=1.6 Hz) 2-141 3.59 (3H, s), 6.41 (1H, s), 6.42 (1H, d, J=15.5 Hz),7.16 (1H, br s), 7.38 (4H, m), 7.52 2H, m , 7.59 1H, dd, J=8.2, 1.7 Hz ,7.75 1H, d, J=15.5 Hz , 8.40 1H, br s 2-142 3.47 (3H, s), 6.29 (1H, s),7.1-7.9 (11H, m), 8.21 (1H, s) 2-143 3.55 (3H, d, J=1.0 Hz), 3.87 (3H,s), 6.38 (1H, s), 6.89 (1H, dd, J=8.9, 2.9 Hz), 7.18 (1H, d, J=8.9 Hz),7.58 (3H, m), 7.79 (1H, dd, J=8.6, 1.7 Hz), 7.90 (4H, m), 8.29 (1H, brs) 2-144 3.54 (3H, d, J=1.0 Hz), 3.87 (3H, s), 6.25 (1H, s), 7.60 (3H,m), 7.8-8.0 (5H, m), 8.30 (1H,brs) 2-145 3.57 (3H, d, J=1.0 Hz), 6.38(1H, s), 7.12 (1H, dd, J=9.3, 2.2 Hz), 7.59 (2H, m), 7.78 (1H, dd,J=8.6, 1.8 Hz), 7.8-8.0 (5H, m), 8.28 (1H, br s) 2-146 1.27 (1.5H, t,J=7.1 Hz), 1.27 (1.5H, t, J=7.1 Hz), 1.62 (3H, d, J=6.7 Hz), 3.53 (3H,s), 4.23 (2H, m), 4.79 (1H, m), 6.35 (1H, s), 6.85 (1H, m), 7.15 (1H, d,J=9.0 Hz), 7.5-7.6 (3H, m), 7.77 (1H, dd, J=8.6, 1.6 Hz), 7.89 (4H, m),8.26 (1H, s) 2-147 0.84 (2H, m), 1.03 (2H, m), 1.50 (1H, m), 3.58 (3H,d, J=1.0 Hz), 6.36 (1H, s), 7.05 (1H, d, J=7.8 Hz), 7.35 (1H, br s),7.88 (1H, br s) 2-148 3.57 (3H, d, J=1.0 Hz), 6.39 (1H, s), 6.61 (1H, t,J=72.7 Hz), 6.88 (1H, dd, J=10.2, 2.6 Hz), 7.59 (2H, m), 7.76 (2H, m),7.90 (3H, m), 8.05 (lh, br s), 8.27 (1H, s) 2-149 3.56 (3H, d, J=1.0Hz), 6.38 (1H, s), 7.43 (1H, d, J=8.4 Hz), 7.6 (3H, m), 7.78 (1H, dd,J=8.6, 1.8 Hz), 7.90 (3H, m), 8.09 (1H, br s), 8.28 (2H, s) 2-150 3.41(3H, d, J=1.1 Hz), 3.71 (1H, s), 3.80 (2H, s), 6.11 (1H, s), 7.1-7.4(6H, m), 8.88 (1H, s) 2-151 3.50 (3H, d, J=1.0 Hz), 3.58 (3H, s), 3.62(2H, s), 6.15 (1H, s), 7.14 (1H, d, J=9.1 Hz), 7.2-7.4 (6H, m) 2-1523.58 (3H, s), 3.90 (3H, s), 4.14 (3H, s), 6.25 (1H, s), 7.21 (1H, d,J=9.0 Hz), 7.26 (1H, s), 7.44 (1H, m), 7.55 (1H, m), 7.76 (1H, m), 7.85(1H, m), 8.58 (1H, s), 10.10 (1H, s) 2-153 3.57 (3H, s), 3.91 (3H, s),4.10 (3H, s), 6.22 (1H, s), 7.22 (1H, d, J=9.0 Hz), 7.23 (1H, s), 7.64(2H, m), 7.91 (1H, m), 7.99 (1H, d, J=8.7 Hz), 8.22 (1H, m), 10.20 (1H,s) 2-154 3.56 (3H, s), 3.87 (3H, s), 4.55 (2H, s), 6.27 (1U, s), 6.82(1H, d, J 8.8 Hz), 7.21 (2H, m), 7.44 (1H, s), 8.72 (1H, s) 2-155 2.52(3H, s), 3.56 (3H, s), 3.90 (3H, s), 6.31 (1H, s), 7.20 (1H, d, J=9.0Hz), 7.55 (2H, m), 7.81 (4H, m), 10.15 (1H, s) 2-156 2.55 (3H, s), 3.52(3H, s), 3.83 (3H, s), 6.22 (1H, s), 7.20 (1H, d, J=9.0 Hz), 7.41 (1H,m), 7.66 (1H, s), 7.79 (3H, m), 8.15 (1H, s), 8.26 (1H, s) 2-157 3.58(3H, s), 3.94 (3H, s), 6.35 (1H, s), 7.25 (1H, d, J=9.0 Hz), 7.61 (2H,m), 7.78 (2H, s), 7.92 (2H, m), 8.04 (1H, s) 2-158 3.55 (3H, s), 3.84(3H, s), 6.24 (1H, s), 7.22 (1H, d, J=9.0 Hz), 7.42 (1H, m), 7.90 (3H,m), 8.14 (1H, s), 8.32 (2H, m) 2-159 3.56 (3H, s), 3.96 (3H, s), 6.35(1H, s), 7.13 (1H, d, J=9.0 Hz), 7.70 (6H, m), 8.15 (1H, s) 2-160 3.55(3H, s), 3.86 (3H, s), 6.24 (1H, s), 7.22 (1H, d, J=9.0 Hz), 7.74 (4H,m), 7.92 (4H, m), 8.10 (4H, m) 2-161 3.55 (3H, s), 3.86 (3H, s), 6.25(1H, s), 7.23 (2H, m), 7.57 (1H, m), 7.72 (1H, m), 7.91 (2H, m), 8.18(1H, s) 2-162 3.55 (3H, s), 3.85 (3H, s), 6.24 (1H, s), 7.23 (1H, d,J=9.0 Hz), 7.49 (1H, m), 7.69 1H, m , 7.90 3H, m , 8.13 1H, sm , 8.342H, m 2-163 3.56 (3H, s), 3.86 (3H, s), 6.25 (1H, s), 7.25 (1H, d, J=9.0Hz), 7.66 (1H, m), 8.05 (3H, m), 8.19 (1H, m), 8.32 (1H, d, J=8.7 Hz),8.39 (1H, s) 2-164 3.35 (3H, s), 3.89 (3H, s), 4.10 (2H, s), 6.37 (1H,s), 7.25 (1H, d, J=9.0 Hz), 8.33 (1H, s) 2-165 3.10 (2H, s), 3.57 (3H,s), 3.90 (2H, s), 4.11 (3H, s), 6.30 (1H, s), 7.20 (1H, d, J=9.0 Hz),7.27 (5H, s), 8.65 (1H, s) 2-166 3.57 (3H, s), 3.90 (SH, s), 4.10 (2H,s), 6.37 (1H, s), 7.25 (1H, d, J=9.0 Hz), 8.15 (1H, s) 2-167 3.50 (3H,s), 3.55 (3H, s), 3.69 (2H, s), 6.16 (1H, s), 7.18 (1H, d, J=9.0 Hz),7.28 (5H, m), 8.33 (1H, s) 2-168 2.14 (3H, s), 3.20 (2H, s), 3.56 (3H,s), 3.88 (3H, s), 6.29 (1H, s), 7.20 (1H, d, J=9.0 Hz), 8.67 (1H, s)2-169 3.36 (3H, s), 3.52 (3H, s), 3.79 (2H, m), 5.96 (1H, s), 7.17 (1H,d, J=9.0 Hz), 7.49 (3H, m), 7.75 (3H, m), 8.75 (1H, m) 2-170 1.28 (3H,t, J=7.1 Hz), 3.32 (2H, s), 3.36 (2H, s), 3.55 (3H, s), 3.88 (3H, s),4.18 (2H, g, J=7.1 Hz), 6.30 (1H, s), 7.21 (1H, d, J=9.0 Hz), 8.33 (1H,s) 2-171 1.26 (3H, t, J=7.1 Hz), 2.62 (2H, m), 2.85 (2H, m), 3.26 (2H,s), 3.56 (3H, s), 3.88 (3H, s), 4.15 (2H, g, J=7.1 Hz), 6.35 (1H, s),7.21 (1H, d, J=9.0 Hz), 8.66 (1H, s) 2-172 1.27 (3H, t, J=7.4 Hz), 2.60(2H, m), 3.27 (2H, s), 3.56 (3H, s), 3.88 (3H, s), 6.28 1H, s , 7.20 1H,d, J=9.0 Hz , 8.73 1H, s 2-173 1.28 (6H, m), 2.97 (1H, m), 3.29 (2H, s),3.57 (3H, s), 3.87 (3H, s), 6.28 (1H, s), 7.20 (1H, d, J=9.0 Hz), 8.79(1H, s) 2-174 0.99 (3H, m), 1.60 (2H, m), 2.53 (2H, m), 3.25 (2H, s),3.57 (3H, s), 3.90 (3H, s), 6.28 (1H, s), 7.20 (1H, d, J=9.0 Hz), 8.80(1H, s) 2-175 3.53 (3H, q, J=3.9 Hz), 3.79 (3H, s), 6.30 (1H, s), 6.90(1H, d, J15.7 Hz), 7.36 (3H, m), 7.53 (4H, m), 9.84 (1H, s) 2-176 3.41(3H, s), 3.79 (3H, s), 6.23 (1H, s), 7.58 (1H, d, J=8.5 Hz), 6.84 (1H,d, J=15.6 Hz), 6.90 (1H, d, J=15.6 Hz), 7.35 (6H, m), 7.50 (4H, m), 7.79(1H, d, J=15.6 Hz), 7.82 (1H, d, J=15.6 Hz) 2-177 3.50 (3H, s), 3.79(3H, s), 6.23 (1H, s), 7.30 (1H, d, J=8.7 Hz), 7.56 (2H, m), 7.85 (4H,m), 8.31 (1H, s), 8.40 (1H, s) 2-178 3.21 (3H, s), 3.88 (3H, s), 6.04(1H, s), 7.59 (SH, m), 7.87 (8H, m), 8.50 (1H, s), 8.57 (1H, s) 2-1793.57 (3H, s), 4.03 (3H, s), 6.29 (1H, s), 6.52 (1H, d, J=15.6 Hz), 7.28(1H, d, J 8.4 Hz), 7.38 (3H, m), 7.47 (2H, m), 7.62 (1H, d, J=15.6 Hz),7.80 (1H, s) 2-180 3.50 (3H, s), 4.00 (3H, s), 6.22 (1H, s) 7.27 (1H, d,J=8.5 Hz), 7.59 (2H, m), 7.87 (4H, m), 8.32 (1H, s), 8.38 (1H, s) 2-1813.52 (3H, s), 3.80 (3H, s),6.23 (1H, s), 7.17 (1H, d, J=9.1 Hz), 7.58(2H, m), 7.87 (4H, m), 8.26 (1H, d, J=55.6 Hz), 8.31 (1H, s) 2-182 3.53(3H, q, J=0.8 Hz), 3.80 (3H, s), 5.41 (1H, d, J=10.9 Hz), 5.87 (1H, d,J=17.6 Hz), 6.23 (1H, s), 6.75 (1H, dd, J=17.6, 10.9 Hz), 7.37 (1H, d,J=8.8 Hz), 7.47 (2H, d, J=8.3 Hz), 7.73 (2H, d, J=8.3 Hz), 8.00 (1H, s)2-183 3.28 (3H, s), 3.80 (3H, s), 5.34 (1H, d, J=11.0 Hz), 5.35 (1H, d,J=11.0 Hz), 5.80 (1H, d, J=17.6 Hz), 5.81 (1H, d, J=17.6 Hz), 6.03 (1H,s), 6.67 (1H, dd, J=17.6, 11.0 Hz), Hz), 7.3-7.6 (10H, m), 7.77 (1H, d,J=15.5 Hz), 7.82 (1H, d, J=15.5 Hz) 2-187 3.78 (3H, s), 3.78 (2H, s),4.58 (2H, s), 4.70 (2H, s), 6.07 (1H, s), 7.14 (1H, d, J=9.1 Hz), 7.35(5H, m), 8.58 (1H, s) 2-188 4.67 (2H, s), 4.76 (2H, d J=5.3 Hz), 6.10(1H, s), 7.26 (1H, d, J=8.8 Hz), 7.57 (2H, m), 7.77 (1H, m), 7.87 (3H,s), 8.19 (1H, m), 8.30 (1H, s) 2-189 1.28 (3H, t, J=7.1 Hz), 3.55 (3H,s), 4.26 (2H, q, J=7.1 Hz), 4.82 (2H, s), 6.22 (1H, s), 7.21 (1H, d,J=8.8 Hz), 7.57 (2H, m), 7.94 (4H, m), 8.52 (1H, s), 10.46 (1H, s) 2-1901.30 (3H, t, J=7.1 Hz), 3.58 (3H, s), 4.31 (2H, q, J=7.1 Hz), 4.78 (2H,s), 6.27 (1H, s), 6.67 (1H, d, J=15.7 Hz), 7.15 (1H, d, J=8.9 Hz), 7.38(3H, m), 7.95 (2H, m), 7.62 (1H, d, J=15.7 Hz) 2-191 1.27 (3H, t, J=7.1Hz), 1.29 (3H, t, J=7.1 Hz), 1.69 (3H, d, J=7.0 Hz), 1.70 (3H, d, J=7.0Hz), 3.56 (3H, s), 3.63 (3H, s), 4.25 (4H, m), 4.95 (2H, m), 6.12 (1H,s), 6.41 (1H, s), 7.19 (2H, d, J=8.9 Hz), 7.56 (4H, m), 7.95 (8H, m),8.54 (1H, s), 8.69 (1H, s), 10.41 (1H, s), 10.65 (1H, s) 2-192 4.95 (2H,s), 6.23 (1H, s), 7.25 (1H, d, J=10.0 Hz), 7.59 (2H, m), 7.87 (4H, s),8.27 (1H, m), 9.28 (1H, s) 2-193 3.56 (3H, q, J=0.5 Hz), 6.40 (1H, s),7.16 (1H, dd, J=8.7, 2.6 Hz), 7.34 (1H, d, J=8.7 Hz), 7.5-7.7 (3H, m),7.7-8.0 (6H, m), 8.10 (1H, dd, J=8.6, 1.6 Hz), 8.18 (1H, br d), 8.27(1H, brs) 2-194 3.53 (3H, q, J=0.8 Hz), 6.36 (1H, s), 7.25 (1H, d, J=9.1Hz), 7.60 (2H, m), 7.76 (1H, dd, J=8.7, 1.8 Hz), 7.90 (3H, m), 8.21 (1H,s), 8.33 (1H, d, J=1.5 Hz) 2-195 2.45 (1H, d, J=2.4 Hz), 3.55 (3H, q,J=0.8 Hz), 4.77 (2H, dd, J=6.1, 2.4 Hz), 6.23 (1H, s), 7.23 (1H, d,J=9.0 Hz), 7.59 (2H, m), 7.90 (4H, m), 8.32 (1H, d, J=0.7 Hz), 8.36 (1H,s) 2-196 1.28 (3H, t, J=7.1 Hz), 3.51 (3H, q, J=0.5 Hz), 4.05 (2H, q,J=7.1 Hz), 6.25 (1H, s), 7.57 (2H, m), 7.88 (4H, m), 8.31 (1H, s), 8.38(1H, s) 2-197 1.20 (3H, t, J=6.2 Hz), 1.29 (3H, t, J=6.2 Hz), 3.54 (3H,q, J=0.6 Hz), 4.43 (1H, q, J=6.2 Hz), 6.23 (1H, s), 7.59 (2H, m), 7.80(1H, m), 7.90 (3H, s), 8.20 (1H, s), 8.30 (1H, s) 2-198 0.89 (3H, t),1.25 (4H, m), 1.53 (2H, m), 2.23 (2H, m), 3.56 (3H, q, J=0.9 Hz), 3.83(3H, s), 6.30 (1H, s), 7.20 (1H, d, J=9.0 Hz), 7.58 (1H, br s) 2-1993.54 (3H, q, J=0.7 Hz), 6.29 (1H, s), 6.73 (1H, dd, J=8.3, 4.5 Hz), 7.43(1H, d, J=9.9 Hz), 7.57 (2H, m), 7.86 (5H, m), 8.21 (1H, dd, J=8.3, 1.7Hz), 8.37 (1H, dd, 14.5, 1.7 Hz), 8.45 (1H, br s) 2-200 3.52 (3H, q,J=1.0 Hz), 4.82 (2H, d, J=‡Hz)~ 6.26 (1H, s), 7.31 (1H, d, J=8.8 Hz),7.59 (2H, m), 7.93 (5H, m), 8.35 (1H, d, J=1.1 Hz) 2-201 2.43 (3H, s),3.54 (3H, q, J=0.9 Hz), 6:36 (1H, s), 7.18 (2H, m), 7.59 (2H, m), 7.8(6H, m), 8.28 (1H, s) 2-202 3.51 (3H, s), 3.87 (3H, s), 6.24 (1H, s),7.12 (1H, d, J=8.8 Hz), 7.42 (1H, d, J=8.8 Hz), 7.59 (2H, m), 7.81 (1H,m), 7.91 (3H, m), 8.06 (1H, s), 8.31 (1H, s) 2-203 3.53 (3H, s), 6.34(1H, s), 7.17 (1H, m), 7.26 (1H, m), 7.57 (2H, m), 7.73 (1H, 2d, J=1.6Hz, 8.6 Hz), 7.88 (4H, m), 8.18 (1H, s), 8.23 (1H, s) 2-204 0.78 (2H,m), 0.97 (2H, m), 1.4 (1H, m), 3.55 (3H, s), 6.34 (1H, s), 7.12 (1H, m),7.24 (1H, m), 7.43 (1H, m), 7.85 (1H, broad) 2-205 3.36 (3H, s), 6.22(1H, s), 7.24 (1H, d, J=8.4 Hz), 7.41 (2H, m), 7.65 (4H, m), 7.86 (1H,2d, J=2.0 Hz, 8.4 Hz), 8.0-8.2 (4H, m), 8.55 (1H, s) 2-206 0.76-0.93(4H, m), 1.50 (1H, m), 3.55 (3H, s), 3.85 (3H, s)6.31 (1H, s), 7.19 (1H,d, J=8.9 Hz), 7.6 (1H, broad) 2-207 3.44 (3H, s), 3.82 (3H, s), 6.24(1H, s), 7.32 (1H, d, J=8.3 Hz), 7.48 (2H, m), 7.6-7.8 (5H, m), 8.10(1H, s), 8.23 (1H, s), 8.78 (1H , s) 3-1 2.74 (3H, d, J=4.7 Hz), 2.76(3H, d, J=4.7 Hz), 3.53 (3H, br q, J=1.3 Hz), 3.83 (3H, s), 6.3 (1H, s),6.66 (1H, m), 7.35 (1H, m), 7.39 (1H, d, J=8.8 Hz) 3-2 0.76 (3H, t,J=7.4 Hz), 1.28 (2H, m), 2.96 (2H, m), 3.57 (3H, s), 3.84 (3H, s), 5.22(1H, m), 6.33 (1H, s), 6.70 (1H, s), 7.14 (1H, d, 19.0 Hz) 3-3 1.22(12H, m), 3.54 (3H, br s), 3.83 (3H, s), 3.86 (2H, m), 6.25 (1H, s),6.45 (1H, s), 7.04 1H,d,J=9.l Hz 3-4 3.52 (3H, s), 3.76 (3H, s), 6.30(1H, s), 6.90-7.25 (6H, m), 7.37 (1H, s), 7.61 (1, s) 3-6 3.46 (3H, s),3.77 (3H, s), 4.19 (2H, m), 5.75 (1H, m), 6.19 (1H, s), 6.90-7.30 (7H,m) 3-7 (rotameric mixture) 1.16 (3H, d, J=6.8 Hz), 1.23 (3H, d, J=6.8Hz), 3.47 (3H, s), 3.53 (3H, s), 3.77 (6H, s), 4.72 (2H, m), 5.72 (2H,m), 6.11 (1H, s), 6.33 (1H, s), 6.95-7.35 (14H, m) 3-8 2.99 (3H, s),3.55 (3H, s), 3.63 (3H, s), 4.38 (1H, d, J=16.2 Hz), 4.58 (1H, d, J=16.2Hz),6.27 (1H, s), 6.58 (1H, s), 7.12 (1H, d, J=9.1 Hz), 7.19 (2H, m),7.33 (3H, m) 3-9 2.31 (3H, s), 3.47 (3H, s), 3.79 (3H, s), 4.17 (2H, m),5.58 (1H, m), 6.18 (1H, s), 6.74 (1H, s), 6.90-7.15 (5H, m) 3-10(CDCl₃+CD₃OD) 3.52 (3H, br s), 3.82 (3H, s), 4.29 (2H, m), 6.23 (1H, s),6.50 (1H, m), 6.70-6.85 (2H, m), 7.14 (1H, d, J=9.0 Hz), 7.22 (1H, m)3-11 2.57 (2H, m), 3.21 (2H, m), 3.54 (3H, s), 3.74 (3H, s), 5.51 (1H,m), 6.27 (1H, s), 7.00- 7.30 (7H, m) 3-12 (CDCl₃+CD₃OD) 1.72 (2H, m),2.58 (2H, m), 3.11 (2H, m), 3.53 (3H, s), 3.85 (3H, s), 5.78 (1H, m),6.28 (1H, s), 7.05-7.35 (7H, m) 3-13 3.55 (3H, s), 3.81 (3H, s), 6.35(1H, s), 7.08 (1H, m), 7.1 (1H, d, J=9.0 Hz), 7.25-7.45 (3H, m),7.55-7.80 (SH, m) 3-23 3.59 (3H, s), 3.64 (3H, s), 4.62 (1H, d, J=14.8Hz), 4.98 (1H, d, J=14.8 Hz), 6.33 (1H, s), 6.47 (1H, s), 6.95-7.50(11H, m) 3-24 3.40 (3H, s), 3.78 (3H, s), 5.88 (1H, m), 5.98 (1H, m),6.12 (1H, s), 7.00-7.30 (12H, m) 3-26 3.56 (3H, s), 3.89 (3H, s), 4.86(2H, s), 6.50 (1H, s), 6.33 (1H, s), 7.25 (1H, d, J= 9.0 Hz) 4-1 3.54(3H, s), 3.64 (3H, s), 3.84 (3H, s), 6.24 (1H, s), 7.25 (1H, s) 4-2 2.87(3H, s), 2.96 (3H, s), 3.53 (3H, s), 3.63 (3H, s), 6.3 (1H, s), 6.85(1H, d, J=8.9 Hz) 4-3 3.51 (3H, d, J=1.0 Hz), 3.95 (3H, s), 6.35 (1H,s), 6.81 (1H, br s), 7.03 (2H, m), 7.22 (1H, d, J=9.0 Hz), 7.23 (1H, m),7.34 (2H, m) 4-4 2.22 (6H, s), 3.50 (3H, d, J=0.5 Hz), 3.94 (3H, ~),6.35 (1H, s), 6.72 (1H, dd, J=8.2, 2.5 Hz), 6.77 (1H, d, J=2.5 Hz), 6.84(1H, br s), 7.07 (1H, d, J=8.2 Hz), 7.20 (1H, d, 19.0 Hz) 4-5 3.49 (3H,d, J=1.0 Hz), 3.83 (3H, s), 5.05 (1H, d, J=12.3 Hz), 5.12 (1H, d, J12.3Hz), 6.20 (1H, s), 6.68 (br s), 7.15 (1H, d, J=9.0 Hz), 7.26-7.37 (5H,m) 4-7 3.50 (3H, br s), 3.82 (3H, s), 5.01 (1H, d, J=12.2 Hz), 5.07 (1H,d, J=12.2 Hz), 6.20 (1H, s), 6.69 (1H, br s), 7.02 (2H, m), 7.17 (1H, d,J=9.0 Hz), 7.28 (2H, m) 4-10 3.48 (3H, br s), 3.99 (3H, s), 6.37 (1H,s), 6.98 (1H, br s), 7.14 (1H, dd, J=8.9, 2.3 Hz), 7.24 (1H, d, J=9.0Hz), 7.43-7.51 (3H, m), 7.37 (7.84 (3H, m) 4-11 1.20-1.85 (10H, m), 3.56(3H, br s), 3.86 (3H, s), 4.57 (1H, m), 6.32 (1H, s), 6.53 (1H, s), 7.17(1H, d, J=9.0 Hz) 4-13 3.54 (3H, d, J=1.1 Hz), 3.78 (3H, s), 6.33 (1H,s), 7.15 (1H, br s), 7.17 (1H, d, J=9.0 Hz), 7.43-7.52 (5H, m) 4-23 3.50(3H, s), 4.75 (2H, m), 5.13 (2H, m), 6.24 (1H, s), 6.54 (1H, s), 7.25(1H, d, J=8.7 Hz), 7.35 (5H, m) 4-24 3.57 (3H, s), 3.86 (3H, s), 5.37(2H, m), 6.30 (1H, s), 6.70 (1H, s), 7.16 (1H, d, J=9.0 Hz), 7.20-7.40(3H, m) 4-25 2.06 (6H, s), 2.25 (3H, s), 3.52 (3H, s), 3.94 (3H, s),6.32 (1H, s), 6.83 (2H, s), 7.09 (1H, br s), 7.20 (1H, d, J=9.0 Hz) 4-262.25 (6H, s), 3.51 (3H, s), 3.83 (3H, s), 5.01 (2H, m), 6.21 (1H, s),6.65 (1H, br s), 7.00-7.20 (4H, m) 4-27 1.30 (9H, s), 3.50 (3H, s), 3.96(3H, s), 6.32 (1H, s), 6.84 (1H, m), 7.10-7.40 (5H, m) 4-28 3.43 (3H,s), 3.82 (3H, s), 5.25 (2H, m), 6.12 (1H, s), 6.73 (1H, br s), 7.16 (1H,d, J=9.0 Hz), 7.30-7.55 (3H., m), 7.70-7.85 (4H, m) 4-29 3.57 (3H, s),3.85 (3H, s), 5.17 (1H, d, J=11.9 Hz), 5.27 (1H, d, J=11.9 Hz), 6.28(1H, s), 6.64 (1H, br s), 6.92 (2H, m), 7.17 (1H, d, J=9.0 Hz), 7.34(1H, m) 4-30 3.49 (3H, s), 3.84 (3H, s), 4.99 (1H, d, J=12.6 Hz), 5.06(1H, d, J=12.6 Hz), 6.23 (1H, s), 6.64 (1H, br s), 7.00-7.25 (4H, m)4-31 1.23 (3H, t, J=7.6 Hz), 2.64 (2H, q, J=7.6 Hz), 3.50 (3H, d, J0.9Hz), 3.83 (3H, s), 5.02 (1H, d, J=12.1 Hz), 5.08 (1H, d, J=12.1 Hz),6.22 (1H, s), 6.67 (1H, br s), 7.10-7.30 (5H, m) 4-32 3.52 (3H, s), 3.85(3H, s), 5.03 (2H, m), 6.24 (1H, s), 6.64 (1H, br s), 7.10-7.21 (2H, m),7.3 8-7.44 (2H, m) 4-33 3.52 (3H, d, J=0.8 Hz), 3.86 (3H, s), 5.22 (1H,d, J=13.2 Hz), 5.31 (1H, d, J=13.2 Hz), 6.22 (1H, s), 6.71 (1H, br s),7.18 (1H, d, J=9.0 Hz), 7.40-7.60 (3H, m), 7.68 (1H, m) 4-34 3.54 (3H,s), 3.88 (3H, s), 5.49 (2H, s), 6.28 (1H, s), 7.24 (1H, d, J=9.0 Hz),7.45-7.70 (3H, m), 8.09 (1H, m) 4-35 3.53 (3H, s), 3.83 (3H, s), 3.84(3H, s), 5.12 (1H, d, J=12.5 Hz), 5.18 (1H, d, J=12.5 Hz), 6.24 (1H, s),6.72 (1H, br s), 6.80-6.95 (2H, m), 7.15 (1H, d, J=9.0 Hz), 7.20- 7.40(2H, m) 4-36 3.51 (3H, d, J=1.0 Hz), 3.87 (3H, s), 5.17 (1H, d, J=13.5Hz), 5.24 (1H, d, J=13.5 Hz), 6.24 (1H, s), 6.89 (1H, br s), 7.18 (1H,d, J=9.0 Hz), 7.20-7.29 (2H, m), 7.68 (1H, m), 8.58 (1H, m) 4-37 2.31(6H, s), 3.52 (3H, s), 3.84 (3H, s), 5.01 (2H, m), 6.23 (1H, s), 6.65(1H, br s), 6.92 (2H, br s), 6.96 (1H, br s), 7.16 (1H, d, J=9.0 Hz)4-38 2.25 (3H, s), 2.31 (3H, s), 3.53 (3H, d, J=0.9 Hz), 3.84 (3H, s),5.04 (1H, d, J=12.2 Hz), 5.09 (1H, d, J=12.2 Hz), 6.25 (1H, s), 6.65(1H, br s), 7.08 (3H, m), 7.16 (1H, d, J=9.0 Hz) 4-39 3.53 (3H, br s),3.86 (3H, s), 5.14 (2H, m), 6.27 (1H, s), 6.70 (1H, br s), 6.90-7.10(3H, m), 7.19 (1H, d, J=9.0 Hz) 4-40 3.51 (3H, d, J=0.9 Hz), 3.81 (3H,s), 3,82 (3H, s), 4.98 (1H, d, J=12.0 Hz), 5.05 (1H, d, J=12.0 Hz), 6.22(1H, s), 6.63 (1H, br s), 6.87 (2H, m), 7.16 (1H, d, J=9.0 Hz), 7.25(2H, m) 4-41 3.53 (3H, d, J=0.9 Hz), 3.83 (3H, s), 4.95 (1H, d, J=12.lHz), 5.01 (1H, d, k12.1 Hz), 5.96 (2H, s), 6.25 (1H, s~, 6.63 (1H, brs), 6.78 (3H, m), 7.17 (1H, d, J=9.0 Hz) 4-42 1.24 (6H, d, J=6.9 Hz),2.91 (1H, m), 3.50 (3H, d, J=0.9 Hz), 3.82 (3H, s), 5.02 (1H, d, J=12.1Hz), 5.08 (1H, d, J=12.1 Hz), 6.23 (1H, s), 6.70 (1H, br s), 7.15 (1H,d, J=9.0 Hz), 7.22 (4H, m) 4-43 3.48 (3H, d, J=1.0 Hz),3.85 (3H, s),5.10 (1H, d, J=13.0 Hz), 5.18 (1H, d, J13.0 Hz), 6.18 (1H, s), 6.72 (1H,br s), 7.18 (1H, d, J=9.0 Hz), 7.41 (2H, m), 7.60 (2H, m) 4-44 3.50 (3H,d, J=1.0 Hz), 3.85 (3H, s), 5.05 (1H, d, J=12.8 Hz), 5.12 (1H, d, J=12.8Hz), 6.22 (1H, s), 6.68 (1H, br s), 6.95-7.10 (3H, m), 7.18 (1H, d,J=9.0 Hz), 7.30 (1H, m) 4-45 3.49 (3H, d, J=0.9 Hz), 3.82 (3H, s), 5.05(1H, d, J=12.6 Hz), 5.11 (1H, d, J=12.6 Hz), 6.21 (1H, s), 6.79 (1H, brs), 7.10-7.20 (3H, m), 7.31-7.36 (2H, m) 4-46 0.89 (4H, br s), 3.54 (3H,d, J=1.0 Hz), 3.75 (3H, s), 4.15 (2H, m), 6.28 (1H, s), 6.56 (1H, br s),7.15 (1H, d, J=9.0 Hz), 7.26 (SH, m) 4-47 1.50 (3H, d, J=6.6 Hz), 3.48(3H, s), 3.84 (3H, s), 5.69 (1H, q, J=6.6 Hz), 5.97 (1H, s), 6.73 (1H,br s), 7.14 (1H, d, J=9.0 Hz), 7.20-7.40 (5H, m) 4-48 3.57 (3H, d, J=0.9Hz), 3.86 (3H, s), 5.19 (1H, d, J=12.3 Hz), 5.25 (1H, d, J=12.3 Hz),6.31 (1H, s), 6.61 (1H, br s), 7.20 (1H, d, J=9.0 Hz) 4-49 3.52 (3H, d,J=0.9 Hz), 5.22 (2H, s), 6.33 (1H, s), 6.53 (1H, br s), 7.00-7.45 (7H,m) 4-50 3.54 (3H, s), 6.36 (1H, s), 6.84 (1H, br s), 7.05-7.45 (8H, m)4-51 2.20 (3H, s), 3.45 (3H, d, J=0.8 Hz), 5.10 (2H, m), 6.22 (1H, s),6.90-7.10 (2H, m), 7.15-7.27 (3H, m) 4-52 2.42 (3H, s), 3.52 (3H, s),6.37 (1H, s), 7.00-7.40 (6H, m) 4-53 2.21 (6H, s), 3.50 (3H, hr d J=0.5Hz), 3.94 (3H, s), 6.35 (1H, s), 6.73 (2H, m), 6.84 (1H, br s), 7.07(1H, d, J=8.1 Hz), 7.20 (1H, d, J=9.0 Hz) 4-54 3.53 (3H, hr d, J=1.1Hz), 3.85 (3H, s), 5.16 (1H, d, J=12.9 Hz), 5.25 (1H, d, J=12.9 Hz),6.24 (1H, s), 6.71 (1H, br s), 7.18 (1H, d, J=9.0 Hz), 7.2-7.4 (4H, m)4-55 2.11 (6H, s), 3.52 (3H, s), 3.95 (3H, s), 6.33 (1H, s), 7.03 (3H,br s), 7.08 (1H, br s), 7.22 (1H, d, J=9.0 Hz) 4-56 3.5 1 (3H, hr d,J=1.l Hz), 3.83 (3H, s), 5.07 (1H, d, J=12.3 Hz), 5.14 (1H, d, J=12.3Hz), 6.23 (1H, s), 6.68 (1H, br s), 7.1-7.3 (4H, m) 4-57 2.88 (2H, t,J=6.5 Hz), 3.55 (3H, s), 3.77 (3H, s), 4.25 (2H, t, J=6.5 Hz), 6.29 (1H,s), 6.52 (1H, br s), 7.1-7.4 (6H, m) 4-58 3.52 (3H, hr d, J=1.0 Hz),3.83 (3H, s), 3.84 (3H, s), 5.12 (1H, d, J=12.5 Hz), 5.17 (1H, d, J=12.5Hz), 6.24 (1H, s), 6.71 (1H, br s), 6.90 (2H, m), 7.15 (1H, d, J=9.0Hz), 7.2- 7.3 (2H, m) 4-59 3.50 (3H, s), 3.74 (6H, s), 6.32 (1H, s),6.56 (2H, d, 18.S Hz), 7.11 (1H, t, J8.S Hz), 7.14 (1H, br s), 7.18 (1H,d, J=9.0 Hz) 4-60 2.34 (3H, s), 3.50 (3H, br d, J=1.1 Hz), 3.83 (3H, s),5.00 (1H, d, J=12.1 Hz), 5.07 (1H, d, J=12.1 Hz), 6.20 (1H, s), 6.64(1H, br s), 7.1-7.2 (5H, m) 4-61 3.50 (3H, hr d, J=1.0 Hz), 3.83 (3H,s), 5.01 (1H, d, J=12.5 Hz), 5.07 (1H, d, J=12.5 Hz), 6.20 (1H, s), 6.66(1H, br s), 7.17 (1H, d, J=9.0 Hz), 7.2-7.3 (4H, m) 4-62 3.53 (3H, hr d,J=1.0 Hz), 3.85 (3H, s), 5.12 (1H, d, J=13.0 Hz), 5.20 (1H, d, J=13.0Hz), 6.25 (1H, s), 6.67 (1H, br s), 7.19 (1H, d, J=9.0 Hz), 7.2-7.3 (2H,m), 7.41 (1H, d, J=1.9 Hz) 4-63 3.51 (3H, hr d, J=1.0 Hz), 3.83 (3H, s),3.88 (3H, s), 3.89 (3H, s), 4.99 (1H, d, J=12.0 Hz), 5.04 (1H, d, J=12.0Hz), 6.20 (1H, s), 6.59 (1H, br s), 6.8-6.9 (3H, m), 7.16 (1H, d, J=9.0Hz) 4-64 3.51 (3H, br d, J=0.9 Hz), 3.86 (3H, s), 5.15 (1H, d, J=13.5Hz), 5.21 (1H, d, J=13.5 Hz), 6.21 (114, s), 6.68 (1H, br s), 7.21 (1H,d, J=9,0 Hz), 7.46 (2H, d, J=8.7 Hz), 8.21 (2H, d, J=8.7 Hz) 4-65 3.50(3H, br d, J1.0 Hz), 3.81 (3H, s), 3.85 (3H, s), 5.02 (1H, d,J=12.511z), 5.10 (1H, 12.5 Hz), 6.21 (1H, s), 6.67 (1H, br s), 6.8-6.9(3H, m), 7.17 (1H, d, J=9.0 Hz), 7.25 (1H, t, J=7.7 Hz) 4-66 3.53 (3H,br d, J=0.9 Hz), 3.82 (3H, s), 4.11 (2H, s), 6.29 (1H, s), 7.04 (1H, brs), 7.20 (1H, d, J=9.0 Hz), 7.25 (5H, m) 4-67 3.52 (3H, brd, J=1.0 Hz),3.86 (3H, s), 5.17 (1H, d, J=13.2 Hz), 5.21 (1H, d, J=13.2 Hz), 6.24(1H, s), 6.65 (1H, br s), 7.20 (1H, d, J=9.0 Hz), 7.53 (1H, t, J=8.0Hz), 7.63 (1H, d, J=8.0 Hz), 8.18 (2H, m) 4-68 2.35 (3H, s), 3.50 (3H,br d, J=1.0 Hz), 3.83 (3H, s), 5.02 (1H, d, J=12.2 Hz), 5.10 (1H, d,J=12.2 Hz , 6.22 1H, s , 6.65 1H, br s , 7.1-7.3 5H, m 4-69 2.27 (3H,s), 2.30 (6H, s), 3.54 (3H, hr d, J=1.1 Hz), 3.83 (3H, s), 5.10 (1H, d,J=11.811z), 5.16 (1H, d, J=11.8 Hz), 6.25 (1H, s), 6.63 (1H, br s), 6.87(2H, s), 7.13 (1H, d, J=9.0 Hz) 4-70 3.55 (3H, hr d, 111.l Hz), 3.83(3H, s), 4.99 (1H, d, J=13.l Hz), 5.08 (1H, d, J=13.1 Hz), 6.27 (1H, s),6.35 (2H, m), 6.63 (1H, br s), 7.17 (1H, d, J=9.0 Hz), 7.41 (1H, m) 5-12.05 (1H, br s), 4.05 (3H, s), 7.66 (1H, d, J=8.8 Hz) 5-2 4.36 (2H, brs), 7.61 (1H, d, J=8.7 Hz) 5-3 2.30 (2H, dt, J=27.2, 5.6 Hz), 3.85 (3H,s), 4.22 (2H, t, J=6.8 Hz), 4.42 (2H, br s), 4.60 (2H, dt, J=46.9, 5.6Hz), 6.65 (1H, d, J=9.5 Hz) 5-4 2.24 (2H, dt, J=26.7, 5.7 Hz), 4.19 (2H,t, J=6.9 Hz), 4.61 (2H, dt, J=47.0, 5.7 Hz), 7.86 (1H, d, J=9.0 Hz) 5-52.30 (2H, dt, J=26.4, 5.7 Hz), 4.17 (2H, t, J=6.8 Hz), 4.55 (2H, dt,J=47.0, 5.7 Hz), 4.88 (2H, br s), 6.55 (1H, d, J=9.6 Hz), 8.07 (1H, hr)5-6 4.06 (3H, s), 7.87 (1H, s) 5-7 2.13 (2H, m), 3.06 (3H, s), 3.93 (2H,t, J=4.8 Hz), 4.60 (2H, hr d, J=47.0 Hz), 7.53 (1H, s) 5-8 2.30 (2H, dt,J=26.4, 5.6 Hz), 4.24 (2H, t, J=6.7 Hz), 4.58 (2H, dt, J=46.8, 5.6 Hz),7.87 (1H, s), 9.62 (1H, s) 5-9 2.06 (1H, s), 2.30 (2H, dtt, J=27.7, 6.8,5.4 Hz), 4.24 (2H, t, J=6.8 Hz), 4.60 (2H, dt, J=46.9, 5.4 Hz), 5.90(2H, s), 6.77 (1H, s) 5-15 2.30 (2H, dtt, J=26.0, 6.1, 5.5 Hz), 2.62(1H, d, J=2.4 Hz), 4.2 1 (2H, t, J=6.8 Hz), 4.48 (2H, s), 4.60 (2H, dt,J=46.9, 5.5 Hz), 4.73 (2H, d, J=2.4 Hz), 6.92 (1H, s) 5-16 1.35 (6H, d,J=6.2 Hz), 2.29 (2H, dtt, J=27.7, 5.9, 5.5 Hz), 4.2 1 (2H, t, J=6.8 Hz),4.29 (2H, br s), 4.53 (1H, g, J=6.2 Hz), 4.59 (2H, dt, J=46.9, 5.5 Hz),6.92 (1H, s) 5-17 2.30 (2H, dt, J=26.4, 5.7 Hz), 2.75 (1H, t, J=2.5 Hz),4.19 (2H, t, J=6.8 Hz), 4.61 (2H, dt, J=47.0, 5.7 Hz), 4.72 (2H, d,J=2.5 Hz), 5.02 (2H, br s), 6.61 (1H, d, J=9.4 Hz) 5-18 1.35 (6H, d,J=6.0 Hz), 2.30 (2H, dtt, J=26.9, 6.8, 5.4 Hz), 4.21 (2H, t, J=6.8 Hz),4.37 (2H, br s), 4.52 (1H, penta, J=6.0 Hz), 4.59 (2H, dt, J=46.5, 5.4Hz), 6.65 (1H, d, J=9.6 Hz) 5-26 2.08 (2H, m), 3.84 (3H, s), 4.09 (2H,t, J=6.7 Hz), 4.31 (2H, dt, J=46.9, 5.6 Hz), 7.26 (1H, d, J=9.1 Hz),7.55 (2H, m), 7.89 (4H, m), 8.40 (1H, s), 8.53 (1H, br s) 5-27 1.67 (2H,dt, 1126.5, 5.8 Hz), 3.86 (3H, s), 3.89 (2H, s), 3.97 (2H, dt, J=42.4,5.6 Hz), 7.27 1H, d, J=8.7 Hz , 7.52 4H, m , 7.78 4H, m , 7.88 4H, m ,8.54 214, s 5-28 2.22 (2H, dt, J=26.2, 5.8 Hz), 3.81 (3H, s), 4.01 (2H,s), 4.13 (2H, d, J=6.8 Hz), 4.52 (2H, dt, J=46.9, 5.6 Hz), 4.64 (2H, s),7.23 (1H, d, J=9.1 Hz), 7.36 (5H, m), 8.67 (1H, br s) 6-1 2.48 (3H, s),7.03 (1H, t, J=57.9 Hz), 7.65 (1H,A, J=8.6 Hz), 9.88 (1H, s) 6-2 2.48(3H, s), 4.25 (2H, br s), 5.70 (1H, br s), 6.59 (1H, d, J=9.4 Hz), 7.07(1H, t, J=58.0 Hz) 6-13 2.53 (3H, s), 6.89 (1H, ddd, J=12.5, 8.3, 2.4Hz), 7.05 (1H, m), 7.10 (1H, t, J=58.0 Hz), 7.33 (1H, d, J=2.2 Hz), 8:21(1H, ddd, J=9.1, 9.1, 6.5 Hz), 8.57 (1H, d, J=2.2 Hz), 8.72 (1H, br d,J=16.5 Hz) 6-14 2.37 (3H, s), 3.88 (3H, s), 6.94 (1H, ddd, J=1 0.9, 8.3,2.3 Hz), 6.99 (1H, m), 7.05 (1H, t, J=58.0 Hz), 7.26 (1H, d, J=9.1 Hz),8.04 (1H, ddd, J=8.8, 8.8, 6.5 Hz~, 8.48 (1H, br d, J=13.4 Hz) 6-15 2.31(3H, s), 3.88 (3H, s), 7.03 (1H, t, J=58.0 Hz), 7.25 (1H, d, J=9.4 Hz),7.60 (2H, m), 7.8-8.0 (4H, m), 8.25 (1H, s), 8.40 (1H, s) 6-16 2.54 (3H,s), 7.12 (1H, d, J=58.0 Hz), 7.35 (1H, d, J=2.3 Hz), 7.61 (2H, m), 7.83(1H, dd, J=8.5, 1.8 Hz), 7.90 (3H, m), 8.29 (1H, s), 8.48 (1H, d, J=2.3Hz), 8.64 (1H, br s) 6-17 2.29 (3H, s), 3.89 (3H, s), 7.03 (1H, t,J=58.0 Hz), 7.53 (1H, s), 7.60 (2H, m), 7.92 (4H, m), 8.07 (1H,brs),8.37 (1H, br s) 6-18 1.29 (3H, t, J=7.l Hz), 2.45 (3H, s), 4.3 (2H, q,J=7.l Hz), 6.7 (1H, broad), 7.03 (1H, t, J=58.0 Hz), 7.83 (1H, s) 6-191.27 (3H, t, J=7.0 Hz), 2.48 (3H, s), 4.18 (2H, q, J=7.0 Hz), 4.51 (2H,s), 6.67 (1H, s), 6.91 (1H, s), 7.08 (1H, t, J=58.0 Hz) 6-20 2.38 (3H,s), 4.77 (4H, s), 7.16 (1H, t, J=57.7 Hz), 7.17 (1H, s) 6-21 2.47 (3H,s), 7.04 (1H, t, J=7.2 Hz), 7.59 (1H, 2d, J=2.3 Hz, 8.6 Hz), 7.91 (1H,t, J=2.1 Hz) 6-22 2.47 (3H, s), 3.65 (2H, s), 6.75 (1H, 2d, J=2.2 Hz,9.4 Hz), 7.07 (1H, t, J=57.9 Hz), 7.20 (1H, t, J=1.8 Hz) 6-23 2.52 (3H,s), 6.9-7.1 (3H, m), 7.10 (1H, t, J=57.9 Hz), 7.14 (1H, 2d), 8.06 (1H,m), 9.76 (1H, s) 6-24 2.51 (3H, s), 6.93 (1H, 2d, J=2.2 Hz, 8.9 Hz),7.12 (1H, t, J=58.0 Hz), 7.12 (1H, s), 7.61 (2H, m), 7.9-8.0 (3H, m),8.07 (1H, 2d, J=1.7 Hz), 8.68 (1H, s), 9.74 (1H, s) 7-1 4.01 (3H, s),4.03 (3H, br g, J=1.0 Hz), 7.43 (1H, d, J=8.4 Hz) 7-2 3.84 (3H, s), 4.06(3H, s), 4.57 (2H, s), 6.57 (1H, d, J=9.3 Hz) 7-3 4.07 (3H, br d, J=0.9Hz), 6.61 (1H, d, J=9.2 Hz) 7-14 3.87 (3H, s), 3.91 (3H, s), 7.23 (1H,d, J=8.9 Hz), 7.60 (2H, m), 7.80-7.96 (4H, m), 8.13 (1H, br s), 8.32(1H, br s) 7-15 3.86 (3H, s), 3.97 (3H, s), 6.45 (1H, d, J=15.6 Hz),7.20 (1H, d, J=8.9 Hz), 7.30-7.52 (6H, m), 7.60 (1H, d, J=15.6 Hz) 8-11.84 (4H, m), 2.44 (4H, m), 7.62 (1H, d, J=8.5 Hz), 9.88 (1H, br) 8-21.79 (4H, m), 2.41 (4H, m), 5.53 (3H, br), 6.53 (1H, d, J=9.1 Hz) 8-31.81 (4H, m), 2.43 (4H, m), 2.58 (1H, t, J=2.4 Hz), 4.24 (2H, br s),4.69 (2H, t, J=2.4 Hz), 6.60 (1H, d, J=9.2 Hz) 8-4 1.35 (6H, d, J=6.2Hz), 1.82 (4H, m), 2.43 (4H, m), 4.11 (2H, br s), 4.48 (1H, q, J=6.2Hz), 6.60 (1H, d, J=9.4 Hz) 8-5 1.77 (4H, m), 1.82 (4H, m), 2.43 (4H,m), 2.34 (4H, m), 4.04 (2H, br s), 4.79 (1H, m), 6.61 (1H, d, J=9.4 Hz)8-6 1.82 (4H, m), 2.42 (4H, m), 4.03 (3H, s), 7.48 (1H, d, J=8.6 Hz) 8-71.80 (4H, m), 2.08 (2H, br s), 2.41 (4H, m), 3.83 (3H, s), 6.60 (1H, d,J=9.4 Hz) 8-8 1.78 (4H, m), 2.38 (4H, m), 3.86 (3H, s), 6.96 (2H, m),7.25 (1H, d, J=9.0 Hz), 8.01 (1H, m), 8.19 (1H, d, J=12.6 Hz) 8-9 1.68(4H, m), 2.32 (4H, m), 3.82 (3H, s), 7.22 (1H, d, J=9.1 Hz), 7.59 (2H,m), 7.91 (5H, m), 8.34 (1H, s) 8-13 1.76 (4H, m), 2.34 (4H, m), 2.37(1H, t, J=2.4 Hz), 4.77 (2H, t, J=2.4 Hz), 6.95 (2H, m), 7.27 (1H, d,J=8.9 Hz), 8.04 (1H, m), 8.38 (1H, hr d, J=12.5 Hz) 8-18 1.28 (6H, d,J=6.2 Hz), 1.76 (4H, m), 2.32 (4H, m), 4.45 (1H, q, J=6.2 Hz), 6.95 (2H,m), 7.24 (1H, d, J=9.0 Hz), 8.00 (1H, m), 8.31 (1H, br d, J=12.7 Hz)8-30 1.71 (4H, m), 2.33 (4H, m), 3.80 (3H, s), 5.39 (1H, d, J=10.9 Hz),5.86 (1H, d, J=17.6 Hz), 6.75 (1H, dd, J=17.6, 10.9 Hz), 7.21 (1H, d,J=9.0 Hz), 7.47 (2H, d, J8.2 Hz), 7.77 (2H, d, J=8.2 Hz), 7.85 (1H, s)8-31 1.76 (4H, m), 2.38 (4H, m), 3.82 (3H, s), 6.52 (1H, d, J=15.6 Hz),7.19 (1H, d, J=9.0 Hz), 7.37 (3H, m), 7.47 (3H, m), 7.65 (1H, d, J=15.6Hz) 8-32 1.85 (4H, m), 2.45 (4H, m), 8.31 (2H, s) 8-33 1.81 (4H, m),2.43 (4H, m), 7.37 (1H, d, J=8.5 Hz), 7.69 (1H, 2d, J=2.3 Hz, 8.5 Hz),8.10 (1H, d, J=2.3 Hz) 8-34 1.86 (4H, m), 2.46 (4H, m), 7.72 (1H, d,J=8.8 Hz), 8.56 (1H, 2d, J=2.6 Hz, 8.8 Hz), 8.92 (1H, d, J=2.6 Hz) 8-351.80 (4H, m), 2.40 (4H, m), 3.83 (2H, s), 6.79 (2H, m), 6.91 (1H, d,J=8.3 Hz). 8-36 1.78 (4H, m), 2.40 (4H, m), 7.15-7.30 (2H, m), 7.6 (2H,m), 7.9 (4H, m), 8.14 (1H, d, J=2.2 Hz), 8.34 (1H, s), 8.59 (1H, s) 9-11.91 (4H, m), 3.67 (4H, m), 7.65 (1H, d, J=8.3 Hz) 9-3 1.87 (4H, m),3.62 (4H, m), 4.03 (3H, s), 7.53 (1H, d, J=8.5 Hz) 9-4 1.88 (4H, m),3.65 (4H, m), 3.85 (3H, s), 4.28 (2H, s), 6.64 (1H, d, J=9.5 Hz) 9-122.01 (4H, m), 3.73 (2H, m), 3.92 (1H, m), 4.15 (1H, m), 7.53 (1H, d,J=8.5 Hz), 7.76 (1H, J=8.5, 2.4 Hz), 8.21 (1H, d, J=2.4 Hz) 9-13 1.90(4H, m), 3.69 (2H, m), 3.95 (2H, m), 4.85 (2H, br s), 6.79 (2H, m), 7.00(1H, d, J=8.3 Hz) 9-14 1.94 (4H, m), 3.69 (2H, m), 4.03 (2H, m), 7.27(2H, m), 7.59 (2H, m), 7.94 (4H, m), 8.19 (1H, d, J=2.0 Hz), 8.47 (1H,s), 9.11 (1H,brs) 9-15 1.70 (4H, m), 3.50 (4H, m), 3.83 (3H, s), 7.23(1H, d, J=9.0 Hz), 7.59 (2H, m), 7.92 (4H, m), 8.34 (1H, s), 8.43 (1H,s) 9-16 1.82 (4H, m), 3.58 (4H, m), 3.87 (3H, s), 6.9-7.1 (2H, m), 7.27(1H, d, J=9.0 Hz), 8.07 (1H, m), 8.49 (1H, d, J=13.1 Hz) 9-17 1.89 (4H,m), 3.65 (4H, m), 7.53 (1H, d, J=8.6 Hz), 7.72 (1H, 2d, J=2.3 Hz, 8.5Hz), 8.13 (1H, d, J=2.3 Hz) 9-18 1.85 (4H, m), 3.63 (4H, m), 4.03 (2H,s), 6.82 (2H, m), 7.09 (1H, 2d, J=0.6 Hz, 8.0 Hz) 9-19 1.80 (4H, m),3.60 (4H, m), 7.22 (1H, 2d, J=2.3 Hz, 8.7 Hz), 7.35 (1H, d, J=8.7 Hz),7.56 (2H, m), 7.89 (4H, m), 8.08 (1H, d, J=2.3 Hz), 8.43 (1H, s), 9.41(1H, s) 11-1 4.05 (3H, s), 7.30 (1H, m), 7.53 (1H, d, J=8.7 Hz), 8.01(1H, d, J=2.1 Hz) 11-2 7.33 (1H, m), 7.70 (1H, d, J=8.4 Hz), 8.06 (1H,d, J=2.1 Hz), 10.29 (1H, s) 11-3 6.53 (1H, d, J=9.5 Hz), 6.53 (3H, br),7.40 (1H, s), 8.17 (1H, s) 11-4 3.86 (3H, s), 4.33 (2H,brs), 6.65 (1H,d, J=9.5 Hz), 7.34 (1H, dq, J=2.2, 1.0 Hz), 8.10 (1H, d, J=2.2 Hz) 11-53.31 (3H, s), 3.79 (3H, s), 4.33 (2H, br s), 7.21 (1H, d, J=1.1 Hz),7.49 (1H, d, J=8.8 Hz), 7.95 (1H, d, J=2.2 Hz) 11-6 3.86 (3H, s), 7.26(1H, d, J=9.2 Hz), 7.27 (1H, dq, J=2.2, 1.1 Hz), 7.56 (2H, m), 7.88 (4H,m), 7.97 (1H, d, J=2.2 Hz), 8.38 (1H, s), 8.79 (1H, s) 11-7 3.93 (3H,s), 7.30 (1H, d, J=8.7 Hz), 7.35 (1H, dq, 12.2, 1.1 Hz), 8.08 (1H, d,J=2.2 Hz) 11-8 1.20, 1.23 (3H, t, J=7.1 Hz), 3.20 (2H, m), 3.94 (3H, s),4.16 (2H, q, J=7.1 Hz), 4.52 (1H, m), 7.32 (2H, m), 8.08 (1H, m) 11-92.43 (3H, g, J=2.1 Hz), 7.67 (1H, d, J=8.5 Hz), 8.01 (1H, s), 10.2 (1H,br) 11-10 2.46 3H, ,J=1.8 Hz,2.63 3H,br,6.60 1H,d,J=9.4 Hz,8.08 1H, s11-11 2.45 (3H, g, J=1.9 Hz), 3.87 (3H, s), 6.66 (1H, d, J=9.6 Hz), 8.06(1H, s) 11-12 2.44 (3H, g, J=1.9 Hz), 2.58 (3H, s), 3.84 (3H, s), 6.60(1H, d, J=9.4 Hz), 8.03 (1H, s) 11-13 2.38 (3H, q, J=1.8 Hz), 3.88 (3H,s), 7.26 (1H, d, J=9.3 Hz), 7.59 (2H, m), 7.80 (1H, m), 7.91 (4H, m),8.11 (1H, s), 8.30 (1H, s) 12-1 1.64 (3H, m), 1.91 (1H, m), 2.10 (1H,m), 2.35 (1H, m), 3.16 (1H, m), 4.17 (1H, m), 4.82 (1H, m), 7.66 (1H, d,J=8.2 Hz), 10.4 (1H, broad) 12-2 1.61 (3H, m), 1.91 (1H, m), 2.10 (1.H,m), 2.38 (1H, m), 3.13 (1H, m), 4.11 (1H, m), 4.14 (2H, s), 4.87 (1H,m), 5.49 (1H, s), 6.64 (1H, d, J=9.0 Hz) 12-3 1.61 (3H, m), 1.90 (1H,m), 2.08 (1H, m), 2.35 (1H, m), 3.10 (1H, m), 4.07 (1H, m), 4.2 (2H,broad), 4.88 (1H, m), 5.5 (1H, broad), 6.63 (1H, d, J9.0 Hz) 12-4 1.60(3H, m), 1.89 (1H, m), 2.09 (1H, m), 2.34 (1H, m), 3.09 (1H, m), 3.85(3H, s), 4.11 (1H, m), 4.3 (2H, broad), 4.87 (1H, m), 6.63 (1H, d, J=9.3Hz) 12-5 1.4-1.7 (3H, m), 1.7-2.4 (3H, m), 2.95 (1H, m), 3.85 (3H, s),3.97 (1H, m), 4.71 (1H, m), 7.26 (1H, m), 7.60 (2H, m), 7.93 (4H, m),8.15 (1H, s), 8.44 (1H, s) 12-6 1.54 (3H, m), 1.78 (1H, m), 2.07 (1H,m), 2.27 (1H, m), 2.95 (1H, m), 4.01 (1H, m), 4.22 (1H, m), 7.44 (1H, d,J=8.S Hz), 7.69 (1H, 2d, J=2.3 Hz, 8.5 Hz), 8.11 (1H, d, J=2.3 Hz) 12-71.50 (3H, m), 1.78 (1H, m), 2.05 (1H, m), 2.28 (1H, m), 2.89 (1H, m),3.90 (1H, m), 3.95 (2H, s), 4.15 (1H, m), 6.81 (2H, m), 6.99 (1H, d,J=7.9 Hz) 12-8 1.41 (3H, m), 1.68 (1H, m), 1.93 (1H, m), 2.24 (1H, m),2.83 (1H, m), 3.88 (1H, m), 4.11 (1H, m), 7.23 (2H, m), 7.54 (2H, m),7.87 (4H, m), 7.97 (1H, s), 8.38 (1H, s), 9.11 (1H, s) 13-1 4.36 (1H, brs), 7.61 (1H, d, J=8.6 Hz), 7.88 (2H, m), 7.99 (2H, m) 13-2 5.42 (1H, brs), 6.58 (1H, d, J=9.4 Hz), 7.95 (4H, m) 13-3 3.86 (3H, s), 7.28 (1H, d,J=9.0 Hz), 7.50-7.95 (IOH, m), 8.03 (1H, br s), 8.28 (1H, br s) 13-43.89 (3H, s), 6.89 (2H, m), 7.30 (1H, d, J=9.0 Hz), 7.70-7.95 (5H, m),8.34 (1H, m) 13-5 7.33 (2H, m), 7.56 (2H, m), 7.7-8.0 (8H, m), 8.19 (1H,d, J=1.4 Hz), 8.32 (1H, s), 8.56 (1H, brs) 14-1 1.23 (3H, t, J=7.1 Hz),2.51 (2H, m), 2.75 (2H, m), 3.55 (3H, s), 3.90 (3H, s), 4.10 (2H, g,J=7.1 Hz), 6.36 (1H, s), 7.20 (1H, d, J=8.9 Hz) 14-2 1.30 (3H, t, J=7.1Hz), 3.56 (3H, s), 3.82 (3H, s), 4.23 (2H, q, J=7.1 Hz), 6.36 (1H, s),6.60 (1H, d, J16.2 Hz), 7.31 (1H, d, J=8.6 Hz), 7.36 (1H, d, J=16.2 Hz)14-3 3.01 (1H, m), 3.25 (1H, m), 3.57 (3H, s), 3.70, 3.73 (3H, 2s),3.93, 3.94 (3H, 2s), 4.55 (1H, m), 6.36, 6.37 (1H, 2s), 7.26 (1H, d,J=8.8 Hz) 14-4 1.23 (3H, t, J=7.1 Hz), 3.03 (1H, m), 3.22 (1H, m), 3.55(3H, s), 3.94 (3H, s), 4.14 (2H, m), 4.51 (1H, m), 6.37 (1H, s), 7.26(1H, d, J=8.8 Hz) 14-5 1.24 (3H, t, J=7.1 Hz), 2.95 (1H, m), 3.31 (1H,m), 3.56 (3H, s), 3.93 (3H, s), 4.16 (2H, m), 4.54 (1H, m), 6.35 (1H,s), 7.26 (1H, d, J=8.8 Hz) 14-6 0.89 (3H, t, J=7.4 Hz), 1.61 (2H, m),3.02 (1H, m), 3.23 (1H, m), 3.56 (3H, s), 3.94 (3H, s), 4.07 (2H, m),4.53 (1H, m), 6.37 (1H, s), 7.25 (1H, d, J=8.8 Hz) 14-7 0.90 (3H, t,J=7.4 Hz), 1.62 (2H, m), 2.96 (1H, m), 3.31 (1H, m), 3.56 (1H, s), 3.94(3H, s), 4.08 (2H, m), 4.56 (1H, m), 6.36 (1H, s), 7.25 (1H, d, ~h8.9Hz) 14-8 0.90 (3H, t, J=7.3 Hz), 1.33 (2H, m), 1.58 (2H, m), 3.03 (1H,m), 3.22 (1H, m), 3.55 (3H, s), 3.94 (3H, s), 4.08 (2H, m), 4.52 (1H,m), 6.37 (1H, s), 7.26 (1H, d, J=8.8 Hz) 14-9 0.91 (3H, t, J=7.3 Hz),1.33 (2H, m), 1.59 (2H, m), 2.98 (1H, m), 3.32 (1H, m), 3.56 (3H, s),3.93 (3H, s), 4.11 (2H, m), 4.56 (1H, m), 6.35 (1H, s), 7.25 (1H, d,J=8.8 Hz) 14-10 0.88 (3H, t, J=6.7 Hz), 1.27 (4H, m), 1.60 (2H, m), 3.02(1H, m), 3.22 (1H, m), 3.56 (3H, s), 3.94 (3H, s), 4.09 (2H, m), 4.52(1H, m), 6.37 (1H, s), 7.25 (1H, d, J=8.9 Hz) 14-11 0.89 (3H, t, J=6.7Hz), 1.31 (4H, m), 1.61 (2H, m), 2.96 (1H, m), 3.30 (1H, m), 3.56 (3H,s), 3.93 (3H, s), 4.10 (2H, m), 4.56 (1H, m), 6.35 (1H, s), 7.26 (1H, d,J=8.9 Hz) 14-12 0.87 (3H, t, J=6.4 Hz), 1.27 (6H, m), 1.59 (2H, m), 3.03(1H, m), 3.22 (1H, m), 3.56 (3H, s), 3.94 (1H, s), 4.08 (2H, m), 4.52(1H, m), 6.37 (1H, s), 7.25 (1H, d, J=8.8 Hz) 14-13 0.88 (3H, t, J=6.9Hz~, 1.28 (6H, m), 1.59 (2H, m), 2.96 (1H, m), 3.32 (1H, m), 3.56 3H,s), 3.94 (3H, s), 4.10 (2H, m), 4.56 (1H, m), 6.35 (1H, s), 7.26 (1H, d,J=8.811z) 14-14 0.88 (6H, m), 1.90 (1H, m), 3.02 (1H, m), 3.23 (1H, m),3.56 (3H, s), 3.87 (2H, m), 3.94 (3H, s), 4.54 (1H, m), 6.37 (1H, s),7.25 (1H, d, J=8.9 Hz) 14-15 0.89 (6H, m), 1.91 (1H, m), 2.96 (1H, m),3.32 (1H, m), 3.56 (3H, s), 3.89 (2H, m), 3.94 (3H, s), 4.58 (1H, m),6.35 (1H, s), 7.26 (1H, d, J8.9 Hz) 14-16 0.89 (6H, m), 1.50 (2H, m),1.60 (1H, m), 3.02 (1H, m), 3.21 (1H, m), 3.56 (3H, s), 3.94 (3H, s),4.13 (2H, m), 4.52 (1H, m), 6.37 (1H, s), 7.25 (1H, d, J=8.911z) 14-170.88 (6H, m), 1.49 (2H, m), 1.62 (1H, m), 2.96 (1H, m), 3.30 (1H, m),3.56 (3H, s), 3.93 (3H, s), 4.14 (2H, m), 4.56 (1H, m), 6.35 (1H, s),7.25 (1H, d, J=8.9 Hz) 14-18 1.44, 1.46 (9H, 2s), 2.90 (1H, m), 3.31(1H, m), 3.56 (3H, s), 3.92, 3.93 (3H, 2s), 4.42 (1H, m), 6.34, 6.37(1H, 2s), 7.26 (1H, d, J=9.0 Hz). 14-19 2.51 (1H, m), 3.05 (1H, m), 3.20(1H, m), 3.56 (3H, s), 3.94 (3H, s), 4.59 (1H, m), 4.68 (2H, m), 6.37(1H, s), 7.26 (1H, d, J=8.9 Hz) 14-20 2.51 (1H, m), 2.99 (1H, m), 3.29(1H, m), 3.56 (3H, s), 3.94 (3H, s), 4.61 (1H, m), 4.70 (2H, m), 6.36(1H, s), 7.26 (1H, d, J=8.911z) 14-21 3.0-3.3 (2H, m), 3.56 (3H, s),3.93, 3.94 (3H, 2s), 4.3-4.6 (2H, m), 4.69 (1H, m), 6.35, 6.37 (1H, 2s),7.28 (1H, d, J8.8 Hz) 14-22 3.06 (1H, m), 3.24 (1H, m), 3.56 (3H, s),3.93, 3.94 (3H, 2s), 4.4-4.6 (2H, m), 5.86 (1H, m), 6.36, 6.37 (1H, 2s),7.28 (1H, d, J=8.8 Hz) 14-23 3.04-3.2 1 (2H, m), 3.56 (3H, s), 4.47,4.65 (2H, 2m), 4.69 (1H, m), 6.37 (1H, s), 7.28 (1H, d, J=8.7 Hz) 14-243.02 (1H, m), 3.24 (1H, m), 3.56 (3H, s), 3.93 (3H, s), 4.61 (2H, m),4.70 (1H, m), 6.35 (1H, s), 7.28 (1H, d, J=8.7 Hz) 14-25 2.98 (1H, m),3.30 (1H, m), 3.34 (3H, s), 3.53 (2H, m), 3.56 (3H, s), 3.94 (3H, s),4.25 (2H, m), 4.62 (1H, m), 6.35 (1H, s), 7.26 (1H, d, J=8.911z) 14-261.18 (3H, m), 3.05 (1H, m), 3.27 (1H, m), 3.4-3.6 (4H, m), 3.56 (3H, s),3.93, 3.94 (3H, 2s), 4.29 (2H, m), 4.61 (1H, m), 6.35, 6.37 (1H, 2s),7.26 (1H, d, J8.811z) 14-27 3.04 (1H, m), 3.21 (1H, m), 3.54 (3H, s),3.91 (3H, s), 4.10 (2H, m), 4.45 (2H, m), 4.61 (1H, m), 6.35 (1H, s),6.92 (3H, m), 7.27 (3H, m) 14-28 2.99 (1H, m), 3.30 (1H, m), 3.55 (3H,s), 3.90 (3H, s), 4.12 (2H, m), 4.46 (2H, m), 4.64 (1H, m), 6.34 (1H,s), 6.93 (3H, m), 7.26 (3H, m) 14-29 2.66 (2H, m), 3.07 (1H, m), 3.21(1H, m), 3.56 (3H, s), 3.95 (3H, s), 4.30 (2H, m), 4.63 (1H, m), 6.35,6.38 (1H, 2s), 7.28 (1H, d, J=8.9 Hz) 14-30 3.08 (1H, m), 3.22 (1H, m),3.56 (3H, s), 3.70 (2H, m), 3.95 (3H, s), 4.30 (1H, m), 4.5l (2H, m),4.65 (1H, m), 6.38 (1H, s), 7.27 (1H, d, J=8.711z). 14-31 3.02 (1H, m),3.42 (1H, m), 3.57 (3H, s), 3.72 (2H, m), 3.95 (3H, s), 4.29 (1H, m),4.52 (2H, m), 4.66 (1H, m), 6.36 (1H, s), 7.27 (1H, d, J=8.811z) 14-321.22 (3H, t, J=7.l Hz), 3.13 (1H, m), 3.31 (1H, m), 3.55 (3H, s), 3.95(3H, s), 4.13 (2H, m), 4.46 (1H, m), 6.38 (1H, s), 7.25 (1H, d,J=8.911z). 14-33 1.23 (3H, t, J=7.111z), 3.08 (1H, m), 3.41 (1H, m),3.57 (3H, s), 3.93 (3H, s), 4.12 (2H, m), 4.49 (1H, m), 6.36 (1H, s),7.25 (1H, d, J=8.911z) 14-34 1.27 (3H, m), 1.61, 1.64 (3H, 2s), 3.20(1H, m), 3.54 (3H, s), 3.61 (1H, m), 3.84 (3H, s), 4.18 (2H, m), 6.32,6.37 (1H, 2s), 7.27 (1H, 2d) 14-35 0.94 (3H, m), 1.62, 1.65 (3H, 2s),1.67 (2H, m), 3.21 (1H, m), 3.54 (3H, s), 3.62 (1H, m), 3.84 (3H, s),4.09 (2H, m), 6.33, 6.37 (1H, 2s), 7.27 (1H, 2d, J=8.811z, 8.8 Hz) 14-360.94 (3H, m), 1.41 (2H, m), 1.61, 1.65 (3H, 2s), 1.63 (2H, m), 3.21 (1H,m), 3.54 (3H, s), 3.60 (1H, m), 3.84 (3H, s), 4.12 (2H, m), 6.32, 6.37(1H, 2s), 7.27 (1H, 2d, J=8.8 Hz, 8.9 Hz) 14-37 0.90 (3H, m), 1.33 (4H,m), 1.61, 1.64 (3H, 2s)., 1.65 (2H, m), 3.20 (1H, m), 3.54 (3H, s), 3.59(1H, m), 3.84 (3H, s), 4.12 (2H, m), 6.32, 6.37 (1H, 2s), 7.27 (1H, 2d,J=8 .9 Hz, 8.7 Hz) 14-38 0.89 (3H, m), 1.30 (6H, m), 1.61~ 1.64 (3H,2s), 1.65 (2H, m), 3.20 (1H, m), 3.54 (3H, s), 3.59 (1H, m), 3.84 (3H,s), 4.11 (2H, m), 6.32, 6.36 (1H, 2s), 7.27 (1H, 2d, J=8.8 Hz, 8.8 Hz)14-39 1.26 (6H, m), 1.59, 1.62 (3H, 2s), 3.20 (1H, m), 3.54 (3H, s),3.63 (1H, m), 3.85 (3H, s), 4.98 (1H, m), 6.32, 6.37 (1H, 2s), 7.27 (1H,2d, J=8.8 Hz, 8.8 Hz) 14-40 0.94 (6H, m), 1.62, 1.65 (3H, 2s), 1.96 (1H,m), 3.21 (1H, m), 3.54 (3H, s), 3.62 (1H, m), 3.84 (3H, s), 3.92 (2H,m), 6.32, 6.37 (1H, 2s), 7.27 (1H, 2d, J8.8 Hz, 8.8 Hz) 14-41 1.63, 1.66(3H, 2s), 3.22 (1H, m), 3.53 (3H, s), 3.63 (1H, m), 3.79 (3H, s), 5.16(2H, m), 6.29, 6.36 (1H, 2s), 7.25 (1H, 2d, J=8.8 Hz, 8.8 Hz), 7.35 (5H,m). 14-42 1.64, 1.67 (3H, 2s), 3.23 (1H, m), 3.52, 3.55 (3H, 2s), 3.66(1H, m), 3.84 (3H, s), 4.71 (1H, m), 5.00 (1H, m), 6.33, 6.37 (1H, 2s),7.18 (1H, m), 7.27 (1H, 2d, J=8.8 Hz, 8.8 Hz) 14-43 1.63, 1.66 (3H, 2s),3.21 (1H, m), 3.54 (3H, s), 3.62 (1H, m), 3.84 (3H, s), 4.63 (2H, m),5.31 (2H, m), 5.89 (1H, m), 6.33, 6.37 (1H, 2s), 7.27 (1H, 2d, J=8.911z,8.7 Hz) 14-44 1.63 (3H, m), 2.52 (1H, m), 3.18 (1H, m), 3.56 (3H, s),3.60 (1H, m), 3.84 (3H, s), 4.74 (2H, m), 6.34, 6.37 (1H, 2s), 7.26,7.27 (1H, 2d, J=8.7 Hz, 8.8 Hz) 14-45 1.65, 1.68 (3H, 2s), 3.19 (1H, m),3.51 (1H, m), 3.55 (3H, s), 3.83 (3H, s), 4.49 (2H, m), 5.86 (1H, m),6.34, 6.37 (1H, 2s), 7.28 (1H, 2d, J=8.811z, 8.8 Hz) 14-46 1.67, 1.68(3H, 2s), 3.18 (1H, m), 3.53, 3.55 (3H, 2s), 3.66 (1H, m), 3.82, 3.83(3H, 2s), 5.73 (1H, m), 6.35, 6.37 (1H, 2s), 7.31 (1H, 2d, J=8.911z, 8.8Hz) 14-47 1.63, 1.65 (3H, 2s), 3.20 (1H, m), 3.36, 3.37 (3H, 2s), 3.55(3H, s), 3.63 (3H, m), 3.84 (3H, s), 4.29 (2H, m), 6.33, 6.36 (1H, 2s),7.27 (1H, 2d, J=8.8 Hz, 8.8 Hz). 14-48 1.62, 1.64 (3H, 2s), 2.16 (3H, t,J=2.4 Hz), 2.73 (2H, m), 3.20 (1H, m), 3.55 (3H, s), 3.59 (1H, m), 3.84(3H, s), 4.30 (2H, m), 6.33, 6.36 (1H, 2s), 7.27 (1H, 2d, J=8.8 Hz, 8.8Hz) 14-49 1.63, 1.65 (3H, 2s), 1.8-2.1 (4H, m), 3.20 (1H, m), 3.54 (3H,s), 3.61 (1H, m), 3.81 (2H, m), 3.84 (3H, s), 4.13 (3H, m), 6.33, 6.36(1H, s), 7.27 (1H, 2d, J=8.7 Hz, 8.9 Hz) 14-50 3.05 (2H, m), 3.29 (1H,m), 3.52, 3.57 (3H, 2s), 3.59 (1H, m), 3.68 (3H, s), 3.76 (3H, s), 3.79,3.80 (3H, 2s), 6.32, 6.35 (1H, 2s), 7.29 (1H, 2d, J=8.911z, 8.8 Hz)14-51 1.31, 1.35 (3H, 2t, J=7.211z, 7.1 Hz), 3.50 (1H, m), 3.55, 3.57(3H, 2s), 3.68 (1H, m), 3.92, 3.94 (3H, 2s), 4.31 (2H, m), 6.35, 6.38(1H, 2s), 7.34 (1H, 2d, J=8.911z, 8.9 Hz) 14-52 1.26 (3H, t, J=7.l Hz),2.48 (3H, s), 3.07 (1H, m), 3.38 (1H, m), 4.21 (2H, q, J=7.l Hz), 4.51(1H, m), 7.07 (1H, t, J=58.0 Hz), 7.23 (2H, m) 14-53 1.24 (3H, t, J=7.lHz), 1.90 (4H, m), 3.15 (1H, m), 3.43 (1H, m), 3.65 (4H, m), 3.92 (3H,s), 4.18 (2H, m), 4.48 (1H, m), 7.26 (1H, d, J10.511z) 14-54 1.16 (3H,t, J=7.2 Hz), 2.36 (3H, s), 3.04 (1H, m), 3.26 (1H, m), 3.48 (3H, s),4.00-4.25 (3H, m.), 6.30 (1H, s), 7.20 (1H, d, J=8.8 Hz) 14-55 1.18 (3H,t, J=7.2 Hz), 2.37 (3H, s), 3.03 (1H, m), 3.31 (1H, m), 3.50 (3H, s),4.00-4.25 (3H, m), 6.28 (1H, s), 7.20 (1H, d, J=8.7 Hz) 14-56 1.21 (3H,t, J=7.2 Hz), 3.10-3.45 (2H, m), 3.90 (3H, s), 4.07 (3H, br d, J=0.9Hz), 4.16 (2H, g, J=7.2 Hz), 4.54 (1H, br t, J=7.3 Hz), 7.20 (1H, d,J=8.6 Hz) 14-57 3.45 (3H, d, J=1.l Hz), 6.21 (1H, s), 7.30 (1H, d, J=8.4Hz), 7.46 (2H, t, J=7.S Hz), 7.5- 7.8 (5H, m) 14-58 3.31 (3H, d,J=0.911z), 6.29 (1H, s), 6.32 (1H, d, J=12.l Hz), 6.80 (1H, d, J=12.1Hz), 7.15 (1H, d, J=8.5 Hz), 7.28 (2H, m), 7.35 (1H, dd, J=8.5, 2.3 Hz),7.42 (2H, m), 7.6- 7.8 (4H, m) 14-59 3.48 (3H, s), 6.34 (1H, s), 6.72(1H, d, J=16.0 Hz), 7.02 (1H, d, J=8.4 Hz), 7.18 (1H, d, J=16.0 Hz),7.30 (1H, dd, J=10.7, 2.3 Hz), 7.39 (2H, m), 7.48 (1H, dd, J=8.7, 1.2Hz), 7.73 (5H, m) 14-60 1.25 (1.5H, t, J=7.l Hz), 1.26 (1,~H, t, J=~7.1Hz), 2.92 (1H, m), 3.26 (1H, m), 3.57 (3H, m), 4.22 (2H, m), 4.36 (1H,m),~6.37 (0.5H, s), 6.38 (0.5H, s), 7.2-7.3 (2H, m) 14-61 1.21 (3H, m),2.49 (3H, s), 3.33 (2H, m), 3.90 (3H, s), 4.18 (2H, m), 4.52 (1H, t,J=7.2 Hz), 7.05 (1H, t, J=58.0 Hz)7.25 (1H, d, J=8.9 Hz) 14-62 1.46 (3H,t, J=z7.0), 3.58 (3H, s), 4.12 (2H, q, J=7.0 Hz), 6.37 (1H, s), 7.26(1H, d, J 8.7 Hz) 14-63 1.22 (3H, t, J=7.2 Hz), 1.47 (3H, t, J=7.0),3.00 (1H, dd, 14.2, 5.2 Hz), 3.23 (1H, dd, J=14.2, 8.4 Hz), 3.55 (3H, q,J=0.8 Hz), 4.12 (2H, q, J=7.0), 4.12 (2H, m), 4.57 (1H, dd, J=8.4, 5.2Hz), 6.37 (1H, s), 7.26 (1H, d, J=8.7 Hz) 14-64 1.23 (3H, t, J=7.1 Hz),1.46 (3H, t, J=7.0 Hz), 2.94 (1H, dd, 14.4, 6.4 Hz), 3.32 (1H, dd,J=14.4, 7.0 Hz), 3.55 (3H, q, J=0.8 Hz), 4.10 (2H, q, J=7.0 Hz), 4.17(2H, q, J=7.1 Hz), 4.61 (1H, dd, J=7.0, 6.4 Hz), 6.34 (1H, s), 7.25 (1H,d, J=8.9 Hz) 14-65 0.89 (3H, t, J=7.3 Hz), 1.46 (3H, t, J=7.0 Hz), 1.62(2H, qt, J=7.3, 6.9 Hz), 3.03 (1H, dd, J=14.2, 5.4 Hz), 3.21 (1H, dd,J=14.2, 8.3 Hz), 3.55 (3H, q, J=1.0 Hz), 4.04 (2H, q, J=7.0 Hz), 4.10(2H, m), 4.59 (1H, dd, J=8.3, 5.4 Hz), 6.37 (1H, s), 7.25 (1H, d, J= 8.8Hz) 14-66 0.90 (3H, t, J=7.3 Hz), 1.46 (3H, t, J=7.0 Hz), 1.63 (2H, qt,J=7.3, 6.9 Hz), 2.94 (1H, dd, J=14.4, 6.8 Hz), 3.32 (1H, dd, J14.4, 6.9Hz), 3.55 (3H, q, J=1.0 Hz), 4.07 (2H, q, J=7.0 Hz), 4.10 (2H, m), 4.64(1H, dd, J=6.9, 6.8 Hz), 6.35 (1H, s), 7.25 (1H, d, 1k 8.9 Hz) 14-671.38 (6H, t, J=6.2), 3.57 (3H, q, J=1.2 Hz), 4.58 (1H, q, J=6.2 Hz),6.37 (1H, s), 7.27 (1H, d, 8.7 Hz) 14-68 1.22 (3H, t, J=7.1 Hz), 1.34,1.39 (6H, t, J=6.2 Hz), 3.03 (1H, dd, J=14.2, 5.3 Hz), 3.26 (1H, dd,J14.2, 8.3 Hz), 3.55 (3H, s), 4.14 (3H, q, J=7.1 Hz), 4.58 (1H, dd,J=8.3, 5.3 Hz), 4.68 (1H, q, J=6.2 Hz), 6.36 (1H, s), 7.25 (1H, d, J=8.9Hz) 14-69 1.22 (3H, t, J7.1 Hz), 1.35, 1.37 (6H, t, 1k6.2 Hz), 2.94 (1H,dd, J=14.4, 6.5 Hz), 3.35 (1H, dd, J=14.4, 7.1 Hz), 3.56 (3H, s), 4.16(3H, q, J=7.1 Hz), 4.64 (1H, q, J=6.2 Hz), 4.66 (1H, dd, J=7.1, 6.5 Hz),6.34 (1H, s), 7.25 (1H, d, J=8.9 Hz) 14-70 1.25 (3H, t, J=7.1 Hz), 2.39(3H, s), 2.89 (1H, dd, J=14.8, 7.8 Hz), 3.23 (1H, dd, J=14.8, 6.1 Hz),3.56 (3H, q, J=4.0 Hz), 4.17 (2H, q, J=7.1 Hz), 4.39 (1H, dd, 1k7.8, 6.1Hz), 6.37, 6.38 (1H, s), 7.00 (1H, d, J=8.0 Hz), 7.22 (1H, d, 1k8.0 Hz),7.27 (1H, s) 14-71 0.89 (3H, m), 1.63 (2H, m), 3.00 (1H, m), 3.30 (1H,m), 3.54, 3.55 (3H, s), 3.93 (3H, s), 4.09 (1H, m), 6.36, 6.38 (1H, s),7.23 (1H, d, J=8.2 Hz), 8.07 (1H, dd, J=8.2, 1.9 Hz), 8.16 (1H, d, J=1.9Hz) 14-72 0.86, 0.88 (3H, t, J=6.8 Hz), 1.57, 1.62 (2H, m), 2.43 (3H,s), 2.96 (1H, dd, J44.2, 6.9 Hz), 3.39 (1H, dd, J=14.2, 7.2 Hz), 3.93(3H, s), 4.05 (2H, m), 4.54 (1H, dd, J=7.2, 6.9 Hz), 7.28, 7.29 (1H, d,J=8.8 Hz), 8.02, 8.04 (1H, s) 14-73 3.14 (2H, m), 3.54 (3H, 2s), 3.94(3H, 2s), 4.63 (1H, m), 6.38 (1H, 2s), 7.25 (1H, d, J=8.9 Hz), 9.5 (1H,broad) 14-74 4.06 (3H, s), 7.47 (1H, d, J=8.4 Hz), 8.10 (1H, m), 8.80(1H, m) 14-75 3.87 (3H, s), 6.61 (1H, d, J=9.4 Hz), 8.12 (1H, m), 8.88(1H, m) 15-1 3.53 3H, s,3.7 2H,broad,6.4 1H,broad,6.29 1H, s,6.681H,d,J=9.l Hz 15-2 0.7-0.9 (4H, m), 1.23 (1H, m), 3.51 (3H, s), 3.87(3H, s), 6.24 (1H, s), 6.47 (1H, s), 6.83 (1H, d, 1k9.0 Hz), 8.02 (1H,s) 15-3 3.02 (3H, s), 3.92 (3H, s), 5.99 (1H, s), 6.74 (1H, s), 6.79(1H, d, J=9.0 Hz), 7.38 (2H, 2d), 7.53 (1H, 2d), 7.72 (2H, d, J=7.2 Hz),8.85 (1H, s) 15-4 3.31 (3H, s), 4.05 (3H, s), 6.20 (1H, s), &86 (2H,~m),6.89 (1H, d, 1h9.l Hz), 7.03 (1H, m), 8.12 (1H, m), 8.23 (1H, m) 15-52.91 (3H, s), 3.91 (3H, s), 5.99 (1H, s), 6.76 (1H, d, J=9.0 Hz), 6.81(1H, s), 7.59 (2H, m), 7.82 (4H, m), 8.32 (1H, s), 8~.98 (1H, s) 15-61.21 (3H, t, J=7.1 Hz), 3.55 (3H, s), 3.95 (3H, s), 4.07 (2H, q, J=7.lHz), 6.28 (1H, bs), 6.31 (1H, s), 6.43 (1H, bs), 6.87 (1H, d, J=9.1 Hz)15-7 3.46 (3H, s), 3.93 (3H, s), 6.29 (1H, s), 6.52 (1H, bs), 6.90 (1H,d, J=9.0 Hz), 7.10 (3H, m), 7.21 (1H, m), 7.34 (2H, m) 15-8 3.28 (3H,s), 3.90 (3H, s), 6.11 (1H, s), 6.66 (1H, s), 6.84 (3H, m), 6.93 (1H, d,J=8.9 Hz), 7.87 (1H, s), 8.07 (1H, m) 15-9 1.33 (3H, t, J=7.1 Hz), 3.16(3H, s), 3.50 (3H, s), 4.05 (3H, s), 4.18 (2H, m), 6.29 (1H, s), 6.68(1H, s), 6.85 (1H, d, J=9.l Hz), 9.73 (1H, s) 15-10 3.54 (3H, s), 3.85(3H, s), 5.40 (2H, m), 5.96 (1H, m), 6.32 (1H, s), 6.72 (1H, d, J=9.2Hz), 7.32 (1H, d), 8.13 (1H, s) 15-11 0.51 (2H, m), 0.82 (2H, m), 1.27(1H, m), 3.56 (3H, s), 3.83 (3H, s), 6.34 (1H, s), 6.67 (2H, m), 7.82(1H, s) 15-12 1.76 (3H, s), 1.80 (3H, s), 3.54 (3H, s), 3.87 (3H, s),6.31 (1H, s), 6.69 (1H, d, J=9.1 Hz), 7.63 (1H, s) 15-13 1.69 (3H, s),3.39 (3H, s), 3.54 (3H, s), 3.83 (3H, s), 4.13 (2H, s), 6.30 (1H, s),6.66 (1H, d, J=9.3 Hz), 9.79 (1H, s) 15-14 2.07 (3H, s), 2.33 (2H, m),2.52 (2H, m), 3.56 (3H, s), 3.86 (3H, s), 6.33 (1H, s), 6.72 (1H, d,J=9.2 Hz), 7.06 (1H, t, J=5.2 Hz), 7.92 (1H, s) 15-15 3.30 (2H, d, J=5.9Hz), 3.52 (3H, s), 3.84 (3H, s), 6.33 (1H, s), 6.72 (1H, d, J=9.1 Hz),7.07 (2H, d, J=7.5 Hz), 7.28 (4H, m), 7.95 (1H, s) 15-16 1.25 (3H, t,J=7.1 Hz), 1.91 (3H, s), 2.98 (2H, 2d), 3.54 (3H, s), 3.89 (3H, s), 4.11(2H, g, J=7.1 Hz), 6.30 (1H, s), 6.74 (1H, d, J=9.1 Hz), 7.76 (1H, s)15-17 1.24 (3H, m), 3.46 (1H, m), 3.50, 3.55 (3H, 2s), 3.84 (3H, s),6.33, 6.37 (1H, 2s), 6.71 (1H, d, J=9.2 Hz), 7.10 (3H, m), 7.28 (3H, m),7.91 (1H, s) 15-18 2.32 (2H, m), 2.81 (2H, m), 3.55 (3H, s), 3.57 (2H,m), 3.94 (3H, s), 6.32 (1H, s), 6.74 (1H, d, J=9.l Hz), 7.18 (4H, m),7.75 (1H, s) 15-19 2.46 (2H, m), 2.91 (2H, m), 3.25 (2H, m), 3.57 (3H,s), 3.87 (3H, s), 6.36 (1H, s), 6.69 (1H, d, J=9.1 Hz), 7.19 (4H, m),7.64 (1H, s) 15-20 3.51 (3H, s), 3.90 (3H, s), 6.35 (1H, s), 6.77 (3H,m), 7.25 (1H, m), 7.83 (1H, s), 8.36 (1H, s) 15-21 3.54 (3H, s), 3.86(3H, s), 6.31 (1H, s), 6.37 (1H, s), 6.79 (1H, d, J=9.3 Hz) 15-22 3.53(3H, s), 3.90 (3H, s), 6.41 (1H, s), 6.74 (1H, d, J=9.2 Hz), 7.39 (1H,m), 7.48 (2H, m), 7.66 (2H, m), 7.80 (3H, m), 8.34 (1H, s) 16-1 3.55(3H, s), 6.36 (1H, s), 6.61 (1H, d, J=2.1 Hz), 7.04 (1H, d, J=2.1 Hz),7.97 (1H, s) 16-2 3.56 (3H, s), 3.81 (3H, s), 6.35 (1H, s), 6.94 (1H, d,J=2.0 Hz), 7.16 (1H, d, J=2.0 Hz) 16-3 3.54 (3H, s), 5.11 (2H, s), 6.34(1H, s), 6.8-6.9 (2H, m), 6.96 (1H, d, J=2.0 Hz), 7.19 (1H, d, J=2.1Hz), 7.25 (1H, m) 16-4 3.53 (3H, s), 6.35 (1H, s), 6.86 (1H, m), 7.00(1H, m), 7.49 (1H, d, J=2.2 Hz), 7.71 (1H, d, J=2.2 Hz), 8.02 (1H, m)16-5 3.42 (3H, s), 6.31 (1H, s), 7.49 (1H, d, J=2.2 Hz), 7.61 (3H, m),7.93 (4H, m), 8.58 (1H, m) 16-6 3.54 (3H, s), 3.86 (3H, s), 6.35 (1H,s), 6.82 (1H, d, J=9.2 Hz), 6.9 (1H, broad) 16-7 3.44 (3H, s), 3.88 (3H,s), 6.26 (1H, s), 7.29 (1H, d, J=8.9 Hz), 7.63 (2H, m), 7.95 (3H, m),8.09 (1H, 2d, J=1.7 Hz, 8.6 Hz), 8.71 (1H, s) 17-1 2.39 (3H, s), 3.56(3H, s), 3.97 (3H, s), 6.37 (1H, s), 7.28 (1H, d, J=9.0 Hz) 17-2 1.15(6H, m), 3.56 (3H, s), 3.73 (2H, m), 3.95 (3H, s), 6.36 (1H, s), 7.28(1H, d, J=9.0 Hz) 17-3 3.51 (3H, s), 4.01 (3H, s), 4.10 (2H, m), 6.32(1H, s), 7.24 (5H, m), 7.30 (1H, d, J=8.6 Hz) 17-4 3.14 (3H, s), 3.83(3H, s), 6.19 (1H, s), 7.46 (8H, m) 17-5 3.14 (2H, m), 3.57 (5H, m),3.96 ~ (3H, s), 6.40 (1H, s), 7.28 (1H, d, J=9.0 Hz)

[0164] The compounds of the present inventions exhibit excellentherbicidal effects when used as an active ingredient of a herbicide. Theherbicide can be used for a wide range of applications, for example oncrop lands such as paddy fields, upland farms, orchards and mulberryfields, and non-crop lands such as forests, farm roads, playgrounds, andfactory sites. The application method may be suitably selected for soiltreatment application and foliar application.

[0165] The compounds of the present invention are capable of controllingnoxious weeds including grass (gramineae) such as bamyardgrass(Echinochloa crus-galli), large crabgrass (Digitaria sanguinalis), greenfoxtail (Setaria viridis), goosegrass (Eleusine indica L.), wild oat(Avena fatua L.), Johnsongrass (Sorghum halepense), quackgrass(Agropyron repens), alexandergrass (Brachiaria plantaginea), paragrass(Panicum purpurascen), sprangletop (Leptochloa chinensis) and redsprangletop (Leptochloa panacea); sedges (or Cyperaceae) such as riceflatsedge (Cyperus iria L.), purple nutsedge (Cyperus rotundus L.),Japanese bulrush (Scirpus Juncoides), flatsedge (Cyperus serotinus),small-flower umbrellaplant (Cyperus difformis), slender spikerush(Eleocharis acicularis), and water chestnut (Eleocharis kuroguwai);alismataceae such as Japanese ribbon wapato (Sagittaria pygmaea),arrow-head (Sagittaria trifolia) and narrowleaf waterplantain (Alismacanaliculatum); pontederiaceae such as monochoria (Monochoria vaginalis)and monochoria species (Monochoria korsakowii); scrophulariaceae such asfalse pimpernel (Linderniapyxidaria) and abunome (Dopatrium Junceum);lythraceae such as toothcup (Rotala indica) and red stem (Ammanniamultiflora); and broadleaves such as redroot pigweed (Amaranthusretroflexus), velvetleaf (Abutilon theophrasti), morningglory (Ipomoeahederacea), lambsquarters (Chenopodium album), prickly sida (Sidaspinosa L.), common purslane (Portulaca oleracea L.), slender amaranth(Amaranthus viridis L.), sicklepod (Cassia obtusifolia), blacknightshade (Solanum nigrum L.), pale smartweed (Polygonum lapathifoliumL.), common chickweed (Stellaria media L.), common cocklebur (Xanthiumstrumarium L.), flexuous bittercress (Cardamine flexuosa WITH.), henbit(Lamium amplexicaule L.) and threeseeded copperleaf (Acalypha australisL.). Accordingly, it is useful for controlling noxious weedsnon-selectively or selectively in the cultivation of a crop plant suchas corn (Zea mays L.), soybean (Glycine max Merr.), cotton (Gossypiumspp.), wheat (Triticum spp.), rice (Oryza saliva L.), barley (Hordeumvulgare L.), oat (Avena saliva L.), sorgo (Sorghum bicolor Moench), rape(Brassica napus L.), sunflower (Helianthus annuus L.), sugar beet (Betavulgaris L.), sugar cane (Saccharum officinarum L.), Japanese lawngrass(Zoysia Japonica stend), peanut (Arachis hypogaea L.) or flax (Linumusitatissimum L.).

[0166] For use as herbicides, the active ingredients of this inventionare formulated into herbicidal compositions by mixing herbicidallyactive amounts with inert ingredients known to the art to facilitateeither the suspension, dissolution or emulsification of the activeingredient for the desired use. The type of formulation preparedrecognizes the facts that formulation, crop and use pattern all caninfluence the activity and utility of the active ingredient in aparticular use. Thus for agricultural use the present herbicidalcompounds may be formulated as water dispersible granules, granules fordirect application to soils, water soluble concentrates, wettablepowders, dusts, solutions, emulsifiable concentrates (EC),microemulsion, suspoemulsion, invert emulsion or other types offormulations, depending on the desired weed targets, crops andapplication methods.

[0167] These herbicidal formulations may be applied to the target area(where suppression of unwanted vegetation is the objective) as dusts,granules or water or solvent diluted sprays. These formulation maycontain as little as 0.1% to as much as 97% active ingredient by weight.

[0168] Dusts are admixtures of the active ingredient with finely groundmaterials such as clays (some examples include kaolin andmontmorillonite clays), talc, granite dust or other organic or inorganicsolids which act as dispersants and carriers for the active ingredient;these finely ground materials have an average particle size of less than50 microns. A typical dust formulation will contain 1% active ingredientand 99% carrier.

[0169] Wettable powders are composed of finely ground particles whichdisperse rapidly in water or other spray carriers. Typical carriersinclude kaolin clays, Fullers earth, silicas and other absorbent,wettable inorganic materials. Wettable powders can be prepared tocontain from 1 to 90% active ingredient, depending on the desired usepattern and the absorbability of the carrier. Wettable powders typicallycontain wetting or dispersing agents to assist dispersion in water orother carriers.

[0170] Water dispersible granules are granulated solids that freelydisperse when mixed in water. This formulation typically consists of theactive ingredient (0.1% to 95% active ingredient), a wetting agent(1-15% by weight), a dispersing agent (1 to 15% by weight) and an inertcarrier (1-95% by weight). Water dispersible granules can be formed bymixing the ingredients intimately then adding a small amount of water ona rotating disc (said mechanism is commercially available) andcollecting the agglomerated granules. Alternatively, the mixture ofingredients may be mixed with an optimal amount of liquid (water orother liquid) and passed through an extruder (said mechanism iscommercially available) equipped with passages which allow for theformation of small extruded granules. Alternatively, the mixture ofingredients can be granulated using a high speed mixer (said mechanismis commercially available) by adding a small amount of liquid and mixingat high speeds to affect agglomeration. Alternatively, the mixture ofingredients can be dispersed in water and dried by spraying thedispersion through a heated nozzle in a process known as spray drying(spray drying equipment is commercially available). After granulationthe moisture content of granules is adjusted to an optimal level(generally less than 5%) and the product is sized to the desired meshsize.

[0171] Granules are granulated solids that do not disperse readily inwater, but instead maintain their physical structure when applied to thesoil using a dry granule applicator. These granulated solids may be madeof clay, vegetable material such as corn cob grits, agglomerated silicasor other agglomerated organic or inorganic materials or compounds suchas calcium sulfate. The formulation typically consists of the activeingredient (1 to 20%) dispersed on or absorbed into the granule. Thegranule may be produced by intimately mixing the active ingredient withthe granules with or without a sticking agent to facilitate adhesion ofthe active ingredient to the granule surface, or by dissolving theactive ingredient in a solvent, spraying the dissolved active ingredientand solvent onto the granule then drying to remove the solvent. Granularformulations are useful where in-furrow or banded application isdesired.

[0172] Emulsifiable concentrates (EC) are homogeneous liquids composedof a solvent or mixture of solvents such as xylenes, heavy aromaticnaphthas, isophorone or other proprietary commercial compositionsderived from petroleum distillates, the active ingredient and anemulsifying agent or agents. For herbicidal use, the EC is added towater (or other spray carrier) and applied as a spray to the targetarea. The composition of an EC formulation can contain 0.1% to 95%active ingredient, 5 to 95% solvent or solvent mixture and 1 to 20%emulsifying agent or mixture of emulsifying agents.

[0173] Suspension concentrate (also known as flowable) formulations areliquid formulations consisting of a finely ground suspension of theactive ingredient in a carrier, typically water or a non-aqueous carriersuch as an oil. Suspension concentrates typically contain the activeingredient (5 to 50% by weight), carrier, wetting agent, dispersingagent, anti-freeze, viscosity modifiers and pH modifiers. Forapplication, suspension concentrates are typically diluted with waterand sprayed on the target area.

[0174] Solution concentrates are solutions of the active ingredient (1to 70%) in solvents which have sufficient solvency to dissolve thedesired amount of active ingredient. Because they are simple solutionswithout other inert ingredients such as wetting agents, additionaladditives are usually added to the spray tank mix before spraying tofacilitate proper application.

[0175] Microemulsions are solutions consisting of the active ingredient(1 to 30%) dissolved in a surfactant or emulsifier, without anyadditional solvents. There are no additional solvents added to thisformulation. Microemulsions are particularly useful when a low odorformulation is required such as in residential turfgrass applications.

[0176] Suspoemulsions are combinations of two active ingredients. Oneactive ingredient is made as a suspension concentrate (1-50% activeingredient) and the second active is made as a emulsifiable concentrate(0.1 to 20%). A reason for making this kind of formulation is theinability to make an EC formulation of the first ingredient due to poorsolubility in organic solvents. The suspoemulsion formulation allows forthe combination of the two active ingredients to be packaged in onecontainer, thereby minimizing packaging waste and giving greaterconvenience to the product user.

[0177] The herbicidal compounds of this invention may be formulated orapplied with insecticides, fungicides, acaricides, nematicides,fertilizers, plant growth regulators or other agricultural chemicals.Certain tank mix additives, such as spreader stickers, penetration aids,wetting agents, surfactants, emulsifiers, humectants and UV protectantsmay be added in amounts of 0.01% to 5% to enhance the biologicalactivity, stability, wetting, spreading on foliage or uptake of theactive ingredients on the target area or to improve the suspensibility,dispersion, redispersion, emulsifiability, UV stability or otherphysical or physico-chemical property of the active ingredient in thespray tank, spray system or target area.

[0178] The compositions of the present invention may be used inadmixture with or in combination with other agricultural chemicals,fertilizers, adjuvants, surfactants, emulsifiers, oils, polymers orphytotoxicity-reducing agents such as herbicide safeners. In such acase, they may exhibit even better effects or activities. As otheragricultural chemicals, herbicides, fungicides, antibiotics, planthormones, plant growth regulators, insecticides, or acaricides may, forexample, be mentioned. Especially with herbicidal compositions havingthe compounds of the present invention used in admixture with or incombination with one or more active ingredients of other herbicides, itis possible to improve the herbicidal activities, the range ofapplication time(s) and the range of applicable weed types. Further, thecompounds of the present invention and an active ingredient of anotherherbicide may be separately formulated so they may be mixed for use atthe time of application, or both may be formulated together. The presentinvention covers such herbicidal compositions.

[0179] The blend ratio of the compounds of the present invention withthe active ingredient of other herbicides can not generally be defined,since it varies depending on the time and method of application, weatherconditions, soil type and type of formulation. However one activeingredient of other herbicide may be incorporated usually in an amountof 0.01 to 100 parts by weight, per one part by weight of the compoundsof the present invention. Further, the total dose of all of the activeingredients is usually from 1 to 10000 g/ha, preferably from 5 to 500g/ha. The present invention covers such herbicidal compositions.

[0180] As the active ingredients of other herbicides, the following(common name) may be mentioned. Herbicidal compositions having thecompounds of the present invention used in combination with otherherbicides, may occasionally exhibit a synergistic effect.

[0181] 1. Those that are believed to exhibit herbicidal effects bydisturbing auxin activities of plants, including a phenoxy acetic acidtype such as 2,4-D, 2,4-DB, 2,4-DP, MCPA, MCPP, MCPB or naproanilide(including the free acids, esters or salts thereof), an aromaticcarboxylic type such as 2,3,6 TBA, dicamba, dichlobenil, a pyridine typesuch as picloram (including free acids and salts thereof), triclopyr orclopyralid and others such as naptalam, benazolin, quinclorac, quinmeracor diflufenzopyr (BAS 654H).

[0182] 2. Those that are believed to exhibit herbicidal effects byinhibiting photosynthesis of plants including a urea type such asdiuron, linuron, isoproturon, chlorotoluron, metobenzuron, tebuthiuronor fluometuron, a triazine type such as simazine, atrazine, cyanazine,terbuthylazine, atraton, hexazinone, metribuzin, simetryn, ametryn,prometryn, dimethametryn or triaziflam, a uracil type such as bromacil,terbacil or lenacil, an anilide type such as propanil or cypromid, acarbamate type such as desmedipham or phenmedipham, ahydroxybenzonitrile type such as bromoxynil or ioxynil, and others suchas pyridate, bentazon and methazole.

[0183] 3. A quaternary ammonium salt type such as paraquat, diquat ordifenzoquat, which is believed to be converted to free radicals byitself to form active oxygen in the plant and thus to exhibit quickherbicidal effects.

[0184] 4. Those which are believed to exhibit herbicidal effects byinhibiting chlorophyll biosynthesis in plants and abnormallyaccumulating a photsensitizing peroxide substance in the plant body,including a diphenyl ether type such as nitrofen, lactofen,acifluorfen-sodium, oxyfluorfen, fomesafen, bifenox, or chlomethoxyfen,a cyclic imide type such as chlorphthalim, flumioxazin, cinidon-ethyl,or flumiclorac-pentyl, and others such as oxadiazon, sulfentrazone,thidiazimin, azafenidin, carfentrazone, isopropazole, fluthiacet-methyl,pentoxazone, pyraflufen-ethyl and oxadiargyl.

[0185] 5. Those which are believed to exhibit herbicidal effectscharacterized by whitening activities by inhibiting chromogenesis ofplants such as carotenoids including a pyridazinone type such asnorflurazon, chloridazon or metflurazon, a pyrazol type such aspyrazolate, pyrazoxyfen or benzofenap, and others such as fluridone,fluramone, diflufencam, methoxyphenone, clomazone, amitrole,sulcotrione, mesotrione, isoxaflutole and isoxachlortole.

[0186] 6. Those which exhibit herbicidal effects specifically togramineous plants including an aryloxyphenoxypropionic acid type (eitheras a mixture of isomers or as a resolved isomer) such asdiclofop-methyl, pyrofenop-sodium, fluazifop butyl or fluazifop-p-butyl,haloxyfop-methyl, quizalofop p-ethyl, quizalafop p-tefuryl, fenoxapropethyl or fenoxaprop-p-ethyl, flamprop-M-methyl or flamprop-m-isopropylor cyhalofop-butyl and a cyclohexanedione type such as alloxydim-sodium,sethoxydim, clethodim, tepraloxydim or tralkoxydim.

[0187] 7. Those which are believed to exhibit herbicidal effects byinhibiting amino acid biosynthesis of plants, including a sulfonylureatype such as chlorimuron-ethyl, nicosulfaron, metsulfuron-methyl,triasulfuron, primisulfuron, tribenuron-methyl, chlorosulfuron,bensulflron-methyl, sulfometuron-methyl, prosulfuron, halosulfuron orhalosulfuron-methyl, thifensulfuron-methyl, rimsulfuron, azimsulfuron,flazasulfuron, imazosulfuron, cyclosulfamuron, flupyrsulfuron,iodosulfuron, ethoxysulfuron, flucarbazone, sulfosulfuron, oxasulfuron atriazolopyrimidinesulfonamide type such as flumetsulam, metosulam,chloransulam or chloransulam-methyl, an imidazolinone type such asimazapyr, imazethapyr, imazaquin, imazamox, imazameth, imazamethabenzmethyl, a pyrimidinesalicylic acid type such as pyrthiobac-sodium,bispyribac-sodium, pyriminobac-methyl or pyribenzoxim (LGC-40863), andothers such as glyphosate, glyphosate-ammonium,glyphosate-isopropylamine or sulfosate.

[0188] 8. Those which are believed to exhibit herbicidal effects byinterfering with the normal metabolism of inorganic nitrogenassimilation such as glufosinate, glufosinate-ammonium, phosphinothricinor bialophos.

[0189] 9. Those which are believed to exhibit herbicidal effects byinhibiting cell division of plant cells, including a dinitroaniline typesuch as trifluralin, oryzalin, nitralin, pendamethalin, ethafluralin,benefin and prodiamine, an amide type such as bensulide, napronamide,and pronamide, a carbamate type such as propham, chlorpropham, barban,and asulam, an organophosphorous type such as amiprofos-methyl orbutamifos and others such as DCPA and dithiopyr.

[0190] 10. Those which are believed to exhibit herbicidal effects byinhibiting protein synthesis of plant cells, including achloroacetanilide type such as alachlor, metolachor (includingcombinations with safeners such as benoxacor, or resolved isomericmixtures of metolachlor including safeners such as benoxacor)propachlor, acetochlor (including combinations with herbicide safenerssuch as dichlormid or MON 4660 or resolved isomeric mixtures ofacetochlor containing safeners such as dichlormid or MON 4660),propisochlor or dimethenamid or an oxyacetamide type such as flufenacet.

[0191] 11. Those in which the mode of action causing the herbicidaleffects are not well understood including the dithiocarbamates such asthiobencarb, EPTC, diallate, triallate, molinate, pebulate, cycloate,butylate, vemolate or prosulfocarb and miscellaneous herbicides such asMSMA, DSMA, endothall, ethofumesate, sodium chlorate, pelargonic acidand fosamine. A few formulation examples of the present invention aregiven as follows. Ingredient Chemical % Trade Name Name SupplierFunction wt./wt. Formulation example 1. Emulsifiable ConcentrateCompound Active 5.0 2-75 Ingredient Toximul Calcium sulfonate and StepanCo. Emulsifier 2.5 H-A nonionic surfactant blend Toximul Calciumsulfonate and Stepan Co. Emulsifier 7.5 D-A nonionic surfactant blendAromatic Aromatic hydrocarbon Exxon Solvent QS 200 Chemical to 100% Co.Formulation example 2. Suspension Concentrate Compound Active 10.00 2-75Ingredient Proylene Anti- 5.00 glycol freeze Antifoam Silicone defoamerDow Anti-foam 0.50 1530 Corning Rhodopol 23 Xanthan gum Rhone- Suspend-0.25 Poulenc ing Aid Morwet Napthalene Witco Corp. Dispersant 3.00 D-425formaldehyde condensate Igepal Octylphenol ethoxylate Rhone- Wetting3.00 CA-720 Poulenc agent Proxel GXL 1,2 benziso-thia- ICI Preser- 0.25zolin-3-one Americas vative Water Diluent 68.00 Formulation example 3.Wettable Powder Compound Active 50.00 2-75 Ingredient GeroponSodium-N-methyl-N- Rhone- Wetting 3.00 T-77 oleoyl taurate Poulenc agentLomar PW Napthalene Sulfonate Henkel Dispersant 5.00 Corp. Kaolin clayKaolin clay J. M. Huber Filler 42.00 Formulation example 4. WaterDispersible Granule Compound Active 50.00 2-75 Ingredient Morwet WitcoCorp. Wetting 2.00 EFW agent Morwet Napthalene Witco Corp. Dispersant10.00 D-425 formaldehyde condensate ASP 400 Kaolin Clay Engelhard Filler38.00 Corp.

[0192] Test Example

[0193] A standard greenhouse herbicide activity screening system wasused to evaluate the herbicidal efficacy and crop safety of these testcompounds. Seven broadleaf weed species including redroot pigweed(Amaranthus retroflexus, AMARE), velvetleaf (Abutilon theophrasti,ABUTH), sicklepod (Cassia obtusifolia, CASOB), ivyleaf morningglory(Ipomoea hederacea, IPOHE), lambsquarters (Chenopodium album, CHEAL),common ragweed (Ambrosia artemisiifolia L., AMBEL), and cocklebur(Xanthium strumarium, XANST) were used as test species. Four grass weedspecies including green foxtail (Setaria viridis, SETVI), barnyardgrass(Echinochloa crus-galli, ECHCG), johnsongrass (Sorghum halepense,SORHA), and large crabgrass (Digitaria sanguinalis, DIGSA) were alsoused. In addition, three crop species, field corn (Zea mays L., var.Dekalb 535, CORN), soybean (Glycine max L., var. Pella 86, SOY), andupland rice (Oryza sp., var.Tebonnet, RICE) were included.

[0194] Pre-emerge test

[0195] All plants were grown in 10 cm square plastic pots which werefilled with a sandy loam soil mix. For pre-emerge tests, seeds wereplanted one day prior to application of the test compounds. Forpost-emerge tests, seeds were planted 8-21 days prior to the test toallow emergence and good foliage development prior to application of thetest substances. At the time of the post-emerge application, plants ofall species were usually at the 2-3 leaf stage of development.

[0196] All test compounds were dissolved in acetone and applied to thetest units in a volume of 187 l/ha. Test materials were applied at ratesranging from 15 g ai/ha to 1000 g ai/ha using a track sprayer equippedwith a TJ8001E even flow flat fan spray nozzle. Plants were arranged ona shelf so that the top of the canopy (post-emerge) or top of the soilsurface (pre-emerge) was 40-45 cm below the nozzle. Pressurized air wasused to force the test solution through the nozzle as it wasmechanically advanced (via electrically driven chain drive) over the topof all test plants/pots. This application simulates a typical commercialfield herbicide application.

[0197] Post-emerge test

[0198] In the post-emerge test, a commercial non-ionic surfactant wasalso included (0.25% v/v) to enhance wetting of the leaf surfaces oftarget plants. Immediately after application, test units of thepre-emerge applications were watered at the soil surface to incorporatethe test materials. Subsequently, these test units were bottom-watered.Post-emerge test units were always bottom-watered.

[0199] At 14 days after application of the test materials, phytotoxicityratings were recorded. A rating scale of 0-100 was used as previouslydescribed in Research Methods in Weed Science, 2nd edition, B. Truelove,Ed., Southern Weed Science Society, Auburn University, Auburn, Alabama,1977. Briefly, “0” corresponds to no damage and “100” corresponds tocomplete death of all plants in the test unit. This scale was used bothto determine efficacy against weed species and damage to crop species.Herbicide activity data for various compounds of this invention, whichare shown by compound No. in Tables 1-8, are shown in Tables 11 and 12.The data demonstrate significant differences between compounds for bothefficacy against weeds and selectivity for crop species. For selectedcompounds, excellent activity against a majority of the weed species wasobserved with minimal damage to at least one of the crop species.

[0200] Following table XIX shows comparative data for the pre-emergeherbicidal activity of compound 1.4 of present invention and thecompound 2 reported in the Japanese patent Toku Kai Hei 5-25144 (1993).The data clearly shows the high level of activity observed with compound1.4.

TABLE XIX Comparative herbicidal activity of compounds 1.4 and 2 Cmpd.Rate no. (gai/ha) AMARE ABUTH CASOB IPOHE CHEAL XANST SETVI ECHCG SORHADIGSA MAIZE SOY RICE 1.4 3.9 30 95 0 0 30 0 0 0 0 0 0 0 0 7.8 100 100 300 60 0 60 0 0 30 0 0 0 15.6 90 100 100 0 100 20 80 0 0 30 0 0 10 31.3100 100 0 50 100 10 80 10 30 30 0 15 20 62.5 100 100 80 90 100 50 100 3040 95 0 40 50 125 100 100 95 100 100 50 100 95 95 100 40 90 60 250 100100 100 100 100 90 100 100 100 100 95 100 65 2 3.9 0 0 0 0 0 0 0 0 0 0 00 0 7.8 0 0 0 0 0 0 0 0 0 0 0 0 0 15.6 0 0 0 0 0 0 0 0 0 0 0 0 0 31.3 00 0 0 0 0 0 0 0 0 0 0 0 62.5 0 0 0 0 0 0 0 0 0 0 0 0 0 125 0 0 30 0 30 00 0 0 0 0 0 0 250 0 50 50 0 50 60 0 0 0 0 0 0 15

[0201] Tables XX and XXI show pre-emerge and post-emerge herbicidalactivity data respectively for a few representative examples of thecompounds described herein. TABLE XX Pre-emerge Herbicidal activityCmpd. Rate no. (gai/ha) AMARE ABUTH CASOB IPOHE CHEAL XANST SETVI ECHCGSORHA DIGSA MAIZE SOY RICE 1-2 63 0 50 90 0 0 — 20 0 0 0 0 0 0 250 0 10100 0 0 — 0 0 0 30 0 0 10 1-4 63 100 100 90 100 100 100 100 100 85 10090 70 60 250 100 100 100 100 100 100 100 100 100 100 100 100 80 1-5 6320 30 0 0 60 0 0 0 0 0 0 0 0 250 95 100 0 10 100 20 90 0 20 70 10 0 101-9 63 100 100 100 100 100 100 100 100 100 100 100 90 95 1-10 63 70 10020 0 30 0 0 0 0 0 0 0 0 250 100 100 50 60 100 60 100 0 0 30 50 0 0 1-1163 100 100 20 20 100 50 80 0 90 90 10 0 20 250 100 100 60 90 100 100 10095 98 100 70 60 70 1-13 63 100 100 80 100 100 100 100 90 95 100 95 60 95250 100 100 100 100 100 100 100 100 100 100 100 95 100 1-15 63 0 20 0 040 — 70 0 0 0 0 0 10 250 20 90 0 0 50 — 80 0 20 90 0 0 30 1-16 63 0 0 00 0 0 0 0 0 0 0 0 0 250 0 0 0 0 70 0 0 0 0 0 0 0 0 1-18 63 100 100 70100 100 — 95 0 70 70 100 40 30 250 100 100 100 100 100 — 99 80 100 90 9590 70 1-19 63 95 100 90 60 100 — 100 90 90 95 60 50 80 250 100 100 100100 100 — 100 100 100 100 70 80 95 1-20 63 100 100 100 40 100 — 80 50 3050 0 15 60 250 100 100 100 100 100 — 100 100 70 90 70 65 70 1-21 63 9870 0 0 100 0 95 0 0 70 0 0 0 250 100 100 0 40 100 100 100 95 90 100 0 010 1-22 63 95 100 0 0 95 — 90 0 0 0 0 0 0 250 100 100 0 20 100 — 100 6060 60 20 10 50 1-30 63 0 50 0 0 85 — 10 0 0 0 0 0 10 250 60 100 70 70100 — 100 0 10 90 20 10 30 1-31 63 80 100 70 0 95 — 50 0 0 0 0 0 0 250100 100 95 80 100 — 100 40 90 90 90 50 10 1-32 63 0 90 40 0 90 0 0 0 0 00 0 20 250 100 100 40 50 100 50 100 95 30 100 20 0 40 1-37 63 100 100 80100 100 — 100 90 90 100 90 15 60 250 100 100 100 100 100 — 100 100 100100 100 90 90 1-38 63 100 100 100 100 100 — 100 95 90 100 80 70 90 250100 100 100 100 100 — 100 100 100 100 90 90 100 1-51 63 90 90 0 50 90 3030 0 10 20 10 0 10 250 100 100 30 80 100 80 90 50 60 90 60 70 70 1-53 63100 100 0 50 100 50 50 0 50 40 50 95 50 250 100 100 50 95 100 90 95 8090 90 90 100 90 1-54 63 100 100 30 100 100 100 90 45 80 80 100 95 60 250100 100 80 100 100 100 100 100 100 100 100 99 95 1-55 63 70 90 0 0 95 —0 10 20 50 0 10 0 250 70 90 0 0 95 — 0 10 20 50 0 10 0 1-59 63 100 10030 100 100 — 30 0 30 30 70 30 30 250 100 100 80 100 100 — 90 70 85 90 9090 70 1-60 63 100 100 70 90 100 — 95 50 80 95 90 50 40 250 100 100 100100 100 — 100 95 100 100 100 95 95 1-61 63 95 100 30 60 100 60 95 75 7040 30 60 50 250 100 100 80 90 100 100 100 99 99 99 90 95 95 1-63 63 100100 20 20 100 — 95 40 50 80 0 10 80 250 100 100 90 95 100 — 100 100 99100 30 90 95 2-1 63 60 100 80 95 90 50 80 10 30 20 50 30 80 250 100 100100 100 100 100 95 70 70 100 100 80 90 2-2 63 100 100 60 90 100 40 90 3060 90 50 10 10 250 100 100 90 100 100 100 100 90 90 95 90 70 50 2-3 63100 100 60 60 100 — 90 0 10 30 40 0 20 250 100 100 100 100 100 — 100 4030 60 80 30 50 2-4 63 80 30 0 20 50 — 0 0 0 0 0 0 0 250 95 100 0 70 100— 80 0 0 50 20 20 10 2-5 63 90 100 40 90 100 — 100 10 60 50 — 10 70 250100 100 100 100 100 — 100 90 90 95 — — 80 2-6 63 0 0 0 0 0 — 0 0 0 0 0 00 250 50 0 0 0 0 — 80 0 20 10 0 0 0 2-7 63 90 100 60 70 100 — 95 40 9095 70 10 60 250 100 100 100 100 100 — 100 100 95 100 95 70 90 2-8 63 400 0 0 60 — 90 0 40 80 60 15 50 250 100 100 0 100 100 — 90 0 40 80 60 1550 2-10 63 50 100 50 60 100 100 40 0 0 90 45 0 0 250 100 100 90 100 100100 100 95 80 95 100 40 30 2-11 63 30 90 0 70 100 — 0 0 0 0 0 0 10 250100 100 60 100 100 — 100 40 50 60 20 10 50 2-12 63 0 50 30 40 0 0 0 0 00 0 0 0 250 0 70 40 70 30 0 0 0 0 0 0 0 0 2-14 63 50 90 0 0 50 — 60 0 00 0 0 0 250 100 100 60 100 100 — 100 0 30 20 60 0 30 2-15 63 0 20 0 2060 0 0 0 0 0 0 0 10 250 80 90 0 30 40 0 0 0 0 0 0 0 0 2-16 63 50 80 0 095 — 0 0 0 0 0 0 0 250 100 100 100 90 100 — 100 40 80 100 0 20 15 2-1863 40 0 0 0 10 — 0 0 0 0 0 0 0 250 100 100 40 40 90 — 80 0 0 0 30 0 202-19 63 80 90 0 10 95 — 20 0 0 40 30 5 10 250 100 100 10 100 100 — 10050 60 100 90 40 60 2-23 63 100 100 70 100 100 100 100 80 60 70 25 60 80250 100 100 100 100 100 100 100 100 90 100 90 100 95 2-24 63 100 100 90100 100 100 100 95 95 100 90 95 90 250 100 100 100 100 100 100 100 100100 100 100 98 99 2-26 63 0 0 0 0 0 0 0 0 0 0 0 0 0 250 80 0 0 0 90 0 00 0 0 0 0 0 2-27 63 100 100 60 80 100 100 100 50 30 95 30 20 70 250 100100 100 100 100 100 100 100 80 100 70 90 90 2-28 63 100 100 5 80 100 —50 0 10 50 10 0 60 250 100 100 100 100 100 — 100 20 50 90 70 10 70 2-2963 100 100 60 30 100 0 100 0 0 60 0 0 40 250 100 100 100 100 100 60 10050 80 90 45 15 65 2-30 63 0 0 0 0 0 0 0 0 0 0 0 0 0 250 0 20 0 0 70 0 200 0 0 0 0 0 2-31 63 100 100 100 100 100 — 100 40 60 90 70 20 40 250 100100 100 100 100 — 100 100 85 100 100 40 90 2-32 63 100 100 95 100 100 —100 99 90 100 90 40 80 250 100 100 100 100 100 — 100 100 100 100 100 9599 2-33 63 100 100 100 100 100 — 100 30 60 100 10 70 70 250 100 100 100100 100 — 100 95 90 100 90 90 80 2-34 63 100 100 100 100 100 100 95 7020 70 15 25 40 250 100 100 100 100 100 100 100 99 85 100 90 90 90 2-3663 100 100 10 0 90 0 25 0 0 0 0 0 0 250 100 100 70 60 100 30 90 10 20 3010 0 40 2-37 63 0 0 0 0 0 0 0 0 0 0 0 0 0 250 30 30 0 0 50 0 0 0 0 0 0 00 2-39 63 100 100 100 95 100 100 100 90 60 99 70 70 90 250 100 100 100100 100 100 100 100 100 100 90 95 99 2-40 63 100 100 80 90 100 100 10085 60 90 95 50 95 250 100 100 100 100 100 100 100 100 100 100 100 95 1002-41 63 100 100 80 90 100 100 95 50 30 70 80 35 50 250 100 100 100 100100 100 100 100 100 100 100 95 90 2-42 63 100 100 80 100 100 100 100 10095 100 100 85 90 250 100 100 100 100 100 100 100 100 100 100 100 98 992-44 63 100 100 60 90 100 100 90 30 50 60 80 10 20 250 100 100 100 100100 100 100 99 95 100 100 70 80 2-45 63 70 0 0 0 60 — 0 0 0 0 0 0 0 250100 70 0 0 90 — 30 0 0 0 0 0 0 2-46 63 100 50 30 0 100 — 90 0 30 30 30 020 250 100 100 100 60 100 — 100 50 90 70 100 90 70 2-47 63 100 100 90100 100 50 100 0 60 100 90 40 70 250 100 100 100 100 100 100 100 99 90100 100 99 95 2-48 63 100 100 100 100 100 100 100 85 95 95 100 90 90 250100 100 100 100 100 100 100 100 95 100 100 99 99 2-49 63 100 100 0 0 100100 80 0 0 20 0 0 20 250 100 100 100 90 100 100 95 10 0 100 40 15 602-50 63 100 100 60 70 100 60 90 10 30 70 90 5 25 250 100 100 100 100 100100 100 100 80 100 100 70 90 2-52 63 100 10 0 0 50 0 40 0 0 0 0 0 0 2-5363 100 100 95 100 100 80 100 40 40 90 95 25 80 250 100 100 100 100 100100 100 99 100 100 100 90 90 2-54 63 100 100 100 85 100 100 100 90 90100 90 90 70 250 100 100 100 100 100 100 100 100 100 100 100 98 90 2-5663 100 100 100 100 100 100 100 90 99 100 40 80 30 250 100 100 100 100100 100 100 100 100 100 90 95 95 2-58 63 100 100 30 20 100 50 100 50 7090 15 40 80 250 100 100 99 100 100 100 100 100 100 100 100 95 95 2-59 63100 100 30 20 100 50 100 40 40 70 10 10 252 250 100 100 100 100 100 90100 9 90 100 100 70 75 2-61 63 100 100 40 90 100 80 10 85 80 90 30 10 75250 100 100 100 100 100 100 100 100 100 100 80 95 95 2-63 63 100 100 100100 100 100 100 95 90 100 95 60 95 250 100 100 100 100 100 100 100 100100 100 100 100 100 2-64 63 90 100 0 0 90 0 100 0 10 40 0 0 10 250 100100 100 40 100 60 100 60 50 70 20 35 60 2-66 63 100 100 35 40 100 0 95 020 60 10 0 10 250 100 100 90 80 100 60 100 60 95 99 20 15 60 2-67 63 100100 100 100 100 100 100 50 80 100 100 90 90 250 100 100 100 100 100 100100 95 100 100 100 99 90 2-69 63 90 100 0 0 100 50 70 0 0 20 0 0 20 250100 100 80 40 100 60 95 10 30 90 0 10 30 2-70 63 70 100 0 0 80 0 0 0 0 00 0 0 250 100 90 40 60 100 30 60 0 0 20 10 0 10 2-72 63 100 100 30 20100 0 60 0 0 30 0 0 10 250 100 100 90 20 100 50 100 50 50 100 50 5 402-73 63 100 100 100 90 100 — 100 90 75 100 40 50 80 250 100 100 100 100100 — 100 100 100 100 100 95 100 2-74 63 100 100 40 0 100 — 70 0 0 20 00 30 250 100 100 70 50 100 — 100 100 100 100 40 15 60 2-75 63 100 100100 20 100 — 100 20 20 70 0 0 30 250 100 100 100 60 100 — 100 100 60 10020 0 80 2-77 63 70 30 0 0 90 — 0 0 0 0 0 0 0 250 100 100 30 30 100 — 600 0 30 20 0 20 2-78 63 100 100 100 20 100 — 90 10 10 30 10 0 40 250 100100 100 100 100 — 100 100 80 100 100 10 95 2-81 63 100 100 90 60 100 —100 70 90 100 70 0 70 250 100 100 100 100 100 — 100 100 90 100 80 90 902-82 63 100 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80 95 90 250 100 100 100 100 100 — 100 100 100 100 100 100100 14-26 63 100 80 0 0 70 — 0 0 0 50 0 0 0 250 100 100 20 0 100 — 99 9570 95 30 50 80 14-27 63 50 0 0 0 0 — 0 0 0 0 0 0 0 250 100 30 0 0 90 — 00 0 90 0 0 0 14-28 63 90 0 0 0 0 — 0 0 0 0 0 0 0 250 100 80 0 0 95 — 020 40 100 40 20 0 14-29 63 20 0 0 0 0 — 0 0 0 0 0 0 0 250 95 80 0 0 50 —0 0 0 50 20 10 20 14-30 63 70 0 0 0 0 — 0 0 0 0 0 0 0 250 100 50 0 0 80— 0 0 0 90 0 0 0 14-31 63 70 0 0 0 40 — 0 0 0 0 0 0 0 250 100 70 0 50 50— 0 0 0 90 20 30 0 14-32 63 100 10 0 0 80 — 0 0 0 20 0 0 0 250 100 50 300 100 — 40 30 20 100 20 0 10 14-33 63 100 20 0 0 0 — 0 0 0 0 0 10 0 250100 90 0 0 90 — 50 0 30 99 20 20 10 14-34 63 100 100 20 10 95 — 30 20 090 30 0 20 250 100 100 10 10 100 — 100 90 30 100 100 25 90 14-35 63 100100 0 0 50 — 80 0 0 50 0 0 0 250 100 100 0 0 100 — 100 99 50 95 20 25 1014-36 63 75 100 0 0 75 10 10 0 0 30 0 0 10 250 100 100 0 0 100 80 95 9030 95 40 10 70 14-37 63 100 90 0 0 100 — 0 0 0 0 0 0 0 250 100 100 0 0100 — 95 99 0 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90 100 100 95 95 14-50 63 100 0 0 10 100 — 0 0 50 00 10 0 250 100 50 30 70 100 — 50 30 95 40 0 90 0 14-51 63 100 100 0 0 90— 0 0 0 0 0 0 0 250 100 100 0 50 100 — 0 0 0 0 0 0 0 14-52 63 40 70 0 080 — 0 0 0 0 0 0 0 250 90 100 0 30 100 — 0 0 0 0 0 0 0 14-54 63 20 0 0 010 0 20 0 0 0 0 0 0 250 85 70 10 40 100 0 80 0 30 30 0 0 15 14-55 63 010 0 0 0 0 0 0 0 0 0 0 0 250 — — — — — — — — — — — — — 14-56 63 100 30 00 80 — 20 0 0 30 0 0 10 250 100 60 10 0 100 — 70 0 30 40 0 0 10 14-57 630 0 0 0 0 — 0 0 0 0 0 0 0 250 0 0 0 0 0 — 0 0 0 20 0 0 0 14-59 63 0 0 00 40 — 0 0 0 0 0 0 0 250 0 0 0 0 0 — 0 0 0 0 0 0 0 14-60 63 100 100 0 90100 — 10 0 0 0 0 0 0 250 100 100 0 100 100 — 60 20 10 30 10 0 20 14-6163 30 0 0 0 0 0 0 0 0 0 0 0 0 250 95 40 0 20 80 0 60 0 20 40 0 0 0 14-6263 40 15 0 0 20 0 0 0 0 0 0 0 0 250 100 95 0 0 80 30 60 20 60 50 0 5 1514-63 63 99 70 0 0 80 0 30 0 0 70 0 0 0 250 100 100 50 0 99 60 99 50 20100 0 0 0 14-64 63 100 90 0 0 60 20 0 0 0 50 0 0 0 250 100 100 0 0 10060 100 95 20 100 0 0 10 14-65 63 100 90 40 40 60 100 20 0 20 90 20 0 0250 100 100 80 70 100 70 90 80 20 100 40 0 0 14-66 63 100 90 0 0 90 0 2050 0 90 0 0 0 250 100 100 0 60 100 0 100 100 30 100 0 0 20 15-1 63 100100 100 100 100 — 100 99 — 100 95 95 90 250 100 100 100 100 100 — 100100 — 100 100 100 100 15-2 63 100 100 100 10 100 — 100 100 100 100 90 8099 250 100 100 100 100 100 — 100 100 100 100 100 100 100 15-3 63 100 100100 100 100 100 100 100 100 100 100 90 95 250 100 100 100 100 100 100100 100 100 100 100 100 100 15-4 63 100 100 100 100 100 — 100 80 — 10090 90 80 250 100 100 100 100 100 — 100 100 — 100 100 100 100 15-5 63 100100 100 100 100 — 100 70 — 100 90 80 70 250 100 100 100 100 100 — 100 99— 100 99 99 99 15-6 63 100 100 90 100 100 — 99 99 100 100 95 95 98 250100 100 100 100 100 — 100 100 100 100 95 100 100 15-7 63 100 100 100 95100 — 100 80 95 90 95 85 90 250 100 100 100 100 100 — 100 100 100 100100 100 100 15-8 63 60 40 20 0 60 — 20 0 — 30 10 0 15 250 100 100 80 70100 — 0 40 — 100 80 90 90 15-9 63 100 100 90 99 100 — 100 99 100 90 10085 95 250 100 100 100 100 100 — 100 100 100 100 100 98 100 15-10 63 100100 80 100 100 100 100 99 100 100 100 75 80 250 100 100 100 100 100 100100 100 100 100 100 100 100 15-11 63 100 100 100 100 100 — 100 100 100100 99 100 100 250 100 100 100 100 100 — 100 100 100 100 100 100 10015-13 46 100 100 100 100 100 — 100 99 99 100 60 35 90 185 100 100 100100 100 — 100 100 100 100 100 100 100 15-14 63 100 100 90 100 100 — 100100 100 100 99 40 99 250 100 100 100 100 100 — 100 100 100 100 100 99100 15-15 63 100 100 100 100 100 — 100 100 100 100 100 95 95 250 100 100100 100 100 — 100 100 100 100 100 100 100 15-16 63 100 100 90 90 100 —100 80 100 100 90 65 90 250 100 100 100 100 100 — 100 100 100 100 100100 100 15-17 63 100 100 100 100 100 — 100 100 100 100 100 80 100 250100 100 100 100 100 — 100 100 100 100 100 95 100 15-18 63 100 100 100 90100 — 95 75 75 100 75 80 90 250 100 100 100 100 100 — 100 100 100 100100 95 99 15-19 63 100 100 100 100 100 — 100 100 100 100 95 80 90 250100 100 100 100 100 — 100 100 100 100 100 100 100 15-20 63 100 100 60 80100 — 100 50 — 100 80 65 70 250 100 100 100 80 100 — 100 100 — 100 95 95100 15-21 63 100 100 100 100 100 — 100 99 100 100 100 95 99 250 100 100100 100 100 — 100 100 100 100 100 100 100 15-22 63 100 100 100 50 100 —90 60 — 100 40 25 30 250 100 100 100 100 100 — 100 100 — 100 90 95 9916-2 63 40 75 0 10 80 — 10 0 0 0 0 0 0 250 100 100 60 50 100 — 60 10 3050 15 0 0 16-6 63 70 90 50 50 90 — 0 0 0 0 20 10 0 250 100 100 70 90 100— 40 50 50 70 60 90 70 16-7 63 0 0 0 0 0 — 0 0 0 0 0 0 0 250 50 0 0 0 0— 0 0 0 0 0 0 0 17-1 63 30 95 0 10 90 — 50 0 0 20 10 0 10 250 90 100 8070 100 — 80 70 60 80 10 10 30 17-2 63 30 0 0 0 60 — 0 0 0 0 0 0 0 250 6020 0 0 90 — 0 0 0 0 0 0 0 17-4 63 30 0 0 0 20 — 0 0 0 0 0 0 0 250 100 6010 10 70 — 20 0 0 10 0 0 10 17-5 63 80 60 0 30 90 — 0 0 0 0 0 0 0 250100 100 30 35 100 — 50 0 20 60 0 0 10

[0202] TABLE XXI Post-emerge Herbicidal Activity Rate AB Cmpd. g AM UTCAS IPO CHE AM SET ECH SOR DIG CO RIC no ai/ha ARE H OB HE AL BEL VI CGHA SA SOY RN E 1-4 63 30 100 60 100 60 50 — 0 0 0 80 0 0 250 95 100 100100 95 90 — 40 70 50 100 20 35 1-5 63 0 10 0 0 0 0 0 0 0 0 10 0 0 250 4060 30 70 50 30 0 0 0 0 50 5 0 1-9 63 100 100 90 100 100 90 90 70 90 90100 30 40 1-10 63 10 30 0 20 10 0 0 0 0 0 0 0 0 250 30 90 10 70 50 30 00 0 0 40 0 0 1-11 63 40 70 0 40 50 10 0 0 0 0 10 0 0 250 60 100 0 70 9510 50 0 0 0 30 0 0 1-13 63 100 100 30 100 100 70 30 30 10 0 80 20 30 250100 100 70 100 100 85 90 70 90 75 100 80 80 1-15 63 0 30 0 0 0 0 0 0 0 00 0 0 250 30 50 0 40 20 0 0 0 0 0 15 0 0 1-16 63 30 30 0 20 30 0 0 0 0 00 0 0 250 70 50 0 50 60 0 0 0 0 0 10 0 0 1-18 63 70 100 30 80 70 — 70 050 50 50 0 0 250 100 100 95 100 100 — 70 0 50 50 100 0 0 1-19 63 30 10010 30 30 — 20 0 0 0 40 5 25 250 70 100 30 95 90 — 95 80 70 10 95 45 801-20 63 90 100 0 100 90 — 0 30 10 10 100 10 20 250 100 100 50 100 100 —60 80 70 20 100 40 50 1-21 63 95 85 10 70 75 10 10 0 0 0 40 5 10 250 100100 30 90 95 30 30 0 0 0 40 5 10 1-22 63 60 100 0 40 40 — 0 0 0 0 30 510 250 80 100 0 90 80 — 80 0 10 0 60 15 40 1-30 63 10 30 0 20 0 0 0 0 00 0 0 0 250 30 100 30 100 60 70 0 0 0 0 20 10 20 1-31 63 10 20 0 10 0 00 0 0 0 0 0 0 250 30 50 0 50 40 0 0 0 0 0 20 0 10 1-32 63 10 30 0 0 0 00 0 0 0 0 0 0 250 30 0 70 60 30 0 0 0 0 10 0 0 1-37 63 90 100 65 100 95— 20 30 10 10 60 10 25 250 100 100 90 100 100 — 80 90 70 70 100 60 601-38 63 80 100 50 80 — — 10 0 0 10 80 25 35 250 100 100 90 100 — — 80 8080 80 100 70 70 1-51 63 70 60 40 40 30 70 0 0 — 10 10 10 10 250 70 80 6095 95 90 30 10 — 20 50 20 30 1-53 63 80 100 60 95 50 — 0 0 0 0 95 0 10250 100 100 95 100 100 — 80 50 40 50 100 30 60 1-54 63 100 100 90 100100 100 40 20 — 40 99 50 40 250 100 100 100 100 100 100 60 75 — 70 10070 45 1-55 63 10 80 10 30 0 70 0 0 0 0 0 0 0 250 10 90 20 95 20 50 40 00 30 20 10 0 1-59 63 95 100 40 100 100 — 10 30 10 0 90 45 30 250 100 100100 100 100 — 70 80 50 40 100 80 60 1-60 63 90 100 50 90 99 — 0 0 0 0 900 10 250 100 100 90 100 100 — 10 20 20 50 100 50 40 1-61 63 50 70 60 10030 70 10 0 — 10 20 10 10 250 70 100 70 100 70 85 30 10 — 30 80 30 351-63 63 10 70 0 95 20 0 0 0 0 0 0 0 10 250 10 100 0 90 50 50 20 30 0 080 0 40 2-1 63 50 100 50 100 95 30 0 0 0 0 90 10 30 250 100 100 100 100100 85 30 10 0 0 100 15 70 2-2 63 90 95 — 95 60 0 0 0 0 0 50 0 20 250100 100 — 100 100 70 30 40 50 30 95 0 60 2-3 63 10 80 0 60 30 — 0 0 0 070 0 0 250 40 100 0 100 30 — 0 0 0 0 90 10 40 2-4 63 0 0 0 0 50 — 0 0 100 30 0 0 250 70 50 0 20 50 — 0 0 10 0 30 0 0 2-5 63 20 90 10 50 40 — 0 00 0 60 5 30 250 40 100 50 90 70 — 0 0 30 0 60 10 40 2-6 63 0 0 0 0 0 — 00 0 0 0 0 0 250 10 70 0 30 30 — 0 0 0 0 5 5 0 2-7 63 10 70 0 50 40 — 0 00 0 70 0 40 250 50 95 30 90 50 — 30 0 0 0 90 10 40 2-8 63 0 0 0 0 0 — 00 0 0 10 0 0 250 20 40 0 50 60 — 0 0 0 0 10 0 0 2-10 63 0 95 0 60 50 0 00 0 0 20 5 0 250 30 100 10 100 90 50 70 60 20 40 65 0 5 2-11 63 0 80 —50 40 — 0 0 0 0 5 5 0 250 30 100 — 60 65 — 20 0 0 0 15 5 0 2-12 63 0 200 0 0 0 0 0 0 0 0 0 0 250 10 65 0 50 40 10 0 0 0 0 0 0 0 2-14 63 40 9010 40 30 — 0 0 0 0 15 0 10 250 70 95 10 80 40 — 0 0 0 0 20 10 30 2-15 630 70 10 40 40 10 0 0 0 0 10 0 0 250 20 90 10 90 60 40 0 0 0 0 30 0 02-16 63 50 100 10 99 80 — 50 90 40 20 70 70 40 250 100 100 80 100 100100 100 100 95 60 100 90 45 2-18 63 0 0 0 0 0 — 0 0 0 0 0 0 0 250 95 4010 30 50 — 0 0 0 0 20 0 0 2-19 63 40 90 0 70 50 — 0 0 0 0 80 0 0 250 75100 10 100 50 30 30 0 0 0 100 0 20 2-23 63 70 100 95 100 70 90 — 0 50 0100 40 50 250 100 100 100 100 90 100 — 30 90 70 100 90 95 2-24 63 100100 100 100 99 100 20 70 60 10 100 70 70 250 100 100 100 100 100 100 7095 90 50 100 95 90 2-26 63 0 0 0 0 0 0 0 0 0 0 0 0 0 250 20 40 0 30 20 00 0 0 0 0 0 0 2-27 63 100 100 50 90 90 60 — 0 20 10 100 50 60 250 100100 90 100 100 90 — 80 85 70 100 95 95 2-28 63 100 100 30 60 60 — 30 0 00 60 15 90 250 100 100 20 50 60 — 30 0 0 0 90 25 90 2-29 63 90 100 20 7580 50 20 0 0 0 60 10 40 250 100 100 40 100 90 60 50 20 10 20 90 25 602-30 63 0 30 0 0 0 0 — 0 0 0 0 0 0 250 20 70 0 20 50 10 — 0 0 0 10 0 02-31 63 100 100 — 90 80 — 10 10 100 90 40 50 250 90 100 — 100 95 — 20 4030 20 95 60 70 2-32 63 100 100 80 100 95 — 0 0 50 0 100 30 30 250 100100 100 100 100 — 90 90 95 70 100 95 80 2-33 63 90 100 70 100 80 70 5010 0 0 60 10 20 250 95 100 80 100 95 95 40 60 20 40 90 40 60 2-34 63 95100 100 75 85 70 — 0 40 10 90 60 65 250 95 100 100 95 90 85 — 30 80 3095 90 85 2-36 63 100 100 60 100 95 80 50 10 10 20 75 10 25 250 100 10060 100 100 95 60 0 10 20 100 20 40 2-37 63 0 0 0 0 0 0 — 0 0 0 0 0 0 25010 30 0 0 20 0 — 0 0 0 10 0 0 2-39 63 70 100 60 99 90 50 20 0 10 0 95 2030 250 95 100 90 100 95 95 80 60 60 50 99 70 70 2-40 63 90 100 50 100 8080 10 0 30 10 100 40 50 250 100 100 90 100 95 100 90 100 100 90 100 9095 2-41 63 95 100 60 100 95 50 20 0 0 0 90 15 10 250 100 100 95 100 10095 30 30 70 20 100 80 70 2-42 63 95 100 65 100 90 70 50 30 10 0 100 1060 250 100 100 100 100 100 95 80 80 95 30 100 60 90 2-44 63 50 100 20 5060 60 0 0 0 0 90 0 0 250 90 100 70 100 90 90 50 10 30 10 100 20 10 2-4563 10 30 0 20 30 — 0 0 0 0 10 0 0 250 20 40 20 30 30 — 40 0 0 0 20 5 102-46 63 30 50 0 0 10 — 0 0 0 0 10 0 10 250 70 100 0 20 — 30 10 0 0 80 2030 2-47 63 90 100 70 70 80 50 20 0 0 0 100 10 20 250 100 100 100 100 10090 30 10 0 0 100 15 45 2-48 63 95 100 50 100 95 85 20 0 30 0 100 50 80250 100 100 100 100 100 100 70 80 60 20 100 70 80 2-49 63 20 90 30 70 6050 — 0 0 0 70 0 0 250 40 100 50 70 60 40 — 0 0 0 60 10 10 2-50 63 90 10080 100 70 40 40 0 0 10 90 10 60 250 100 100 90 100 90 65 60 30 40 30 9070 65 2-52 63 30 30 0 10 10 20 0 0 0 0 0 0 0 2-53 63 90 100 70 90 95 7020 0 0 0 100 10 30 250 100 100 100 100 100 90 40 70 50 20 100 70 70 2-5463 100 100 90 100 100 90 10 20 50 10 100 80 90 250 100 100 100 100 100100 50 90 80 20 100 80 95 2-56 63 100 100 100 100 100 70 80 0 0 0 100 3045 250 100 100 100 100 100 100 60 50 60 30 100 80 90 2-58 63 100 100 10095 100 100 50 20 20 10 100 40 50 250 100 100 100 100 100 100 60 90 90 40100 90 85 2-59 63 100 100 90 100 100 70 20 0 30 0 75 70 70 250 100 100100 100 100 100 20 30 65 30 90 80 80 2-61 63 100 100 100 100 100 100 6040 20 20 100 35 60 250 100 100 100 100 100 95 90 70 70 50 100 90 90 2-6363 100 100 100 100 99 80 50 10 20 0 100 50 70 250 100 100 100 100 100100 95 100 100 70 100 95 95 2-64 63 85 100 40 70 80 60 20 30 20 10 50 5060 250 100 100 70 90 100 90 50 40 20 20 60 60 90 2-66 63 100 100 160 100100 100 90 70 10 10 95 15 50 250 100 100 70 90 100 75 80 50 50 20 90 7090 2-67 63 100 100 100 99 100 100 20 0 0 0 100 20 70 250 100 100 100 100100 100 30 40 80 40 100 95 80 2-69 63 40 100 10 50 50 40 0 0 0 0 20 0 0250 50 100 30 40 60 30 0 0 0 0 30 0 0 2-70 63 70 100 10 60 50 30 20 0 00 10 0 0 250 70 100 20 60 70 30 0 0 0 0 20 0 0 2-72 63 70 100 70 50 7070 — 0 0 0 15 0 0 250 90 100 95 60 80 60 — 0 0 0 30 10 20 2-73 63 100100 60 100 70 100 50 30 10 30 95 25 20 250 100 100 100 100 95 100 90 6050 30 100 50 70 2-74 63 95 100 30 60 70 70 0 0 0 0 60 0 25 250 100 10070 60 70 95 20 0 0 0 100 15 50 2-75 63 100 100 100 100 100 — 30 10 20 0100 10 70 250 100 100 100 100 100 — 80 50 40 20 100 15 80 2-77 63 10 10040 60 100 — 0 0 0 0 40 0 20 250 100 100 100 95 80 — 0 0 0 0 90 10 402-78 63 100 100 70 80 100 — 30 10 0 0 80 25 50 250 100 100 100 100 100 —30 10 10 0 100 30 65 2-81 63 100 100 70 100 90 — 40 50 20 20 90 30 60250 100 100 100 100 100 — 60 90 80 80 100 90 90 2-82 63 100 100 100 6090 — 40 20 0 0 60 10 50 250 100 100 100 90 90 — 50 30 30 30 50 25 402-83 63 40 50 0 10 20 — 0 0 0 0 10 0 100 250 90 70 0 20 50 — 0 0 0 0 100 0 2-84 63 80 30 20 30 30 — 30 0 0 0 10 10 0 250 100 100 100 70 80 — 00 0 0 70 10 20 2-86 63 100 100 100 100 100 — 90 90 70 30 100 90 80 250100 100 100 100 100 — 100 100 100 95 100 100 100 2-87 63 100 100 40 10080 — 30 10 10 10 95 30 40 250 100 100 100 100 90 — 40 50 50 50 100 80 752-89 63 70 100 50 90 60 — 20 0 0 0 80 0 60 250 100 100 60 100 90 — 20 1010 0 99 0 70 2-92 63 20 100 0 20 20 — 0 0 0 0 10 0 10 250 50 100 30 10080 — 0 0 0 0 80 30 60 2-98 63 75 100 100 100 70 80 — 0 0 0 100 20 40 250100 100 100 100 90 100 — 20 90 50 100 90 90 2-100 63 80 100 70 100 80 7060 0 0 0 100 15 45 250 100 100 60 100 80 90 70 30 60 20 100 80 70 2-10263 0 0 0 0 0 — 0 0 0 0 0 0 0 250 40 30 0 0 0 — 0 0 0 0 40 0 0 2-105 63100 100 80 100 80 100 70 10 0 0 100 0 0 250 100 100 80 100 90 100 100 3030 10 100 10 30 2-115 63 100 100 90 90 100 — 0 10 0 20 50 5 20 250 100100 95 95 100 — 0 20 0 50 50 5 50 2-117 63 10 80 40 90 — — 0 0 0 0 30 510 250 70 100 95 100 — — 0 0 0 0 90 20 40 2-118 63 30 60 0 50 — — 0 0 00 40 10 10 250 30 80 30 90 — — 0 0 0 0 90 20 10 2-119 63 90 100 30 10080 — 40 40 60 30 100 70 60 250 100 100 60 100 100 — 90 90 90 80 95 90 902-120 63 90 100 30 100 80 — 20 40 40 10 70 50 50 250 100 100 30 100 80 —60 30 50 60 90 70 90 2-121 63 90 70 10 100 60 — 0 0 0 25 0 10 15 250 100100 60 100 80 — 20 0 10 10 60 20 25 2-122 63 100 100 100 100 100 — 90 3030 40 90 40 35 250 100 100 100 80 100 — 95 50 60 60 100 40 60 2-123 63100 100 100 100 100 — 20 10 10 10 70 35 60 250 100 100 100 100 100 — 3020 30 30 95 40 70 2-124 63 30 40 0 20 30 — 0 0 0 0 15 0 0 250 90 95 2030 50 — 0 0 0 0 15 5 0 2-125 63 100 100 90 100 100 — 40 20 30 20 90 1040 250 100 100 100 100 100 — 40 20 30 20 90 10 40 2-126 63 80 90 60 8080 — 30 0 0 20 30 10 10 250 100 100 60 100 95 — 40 10 10 30 60 10 502-127 63 100 100 100 100 70 — 30 30 20 20 35 10 30 250 100 100 60 95 100— 40 20 20 30 70 15 35 2-128 63 100 100 60 100 100 — 50 10 — 10 60 5 10250 100 100 80 100 100 — 60 20 — 35 60 15 — 2-129 63 100 100 80 100 100— 80 30 — 30 100 70 35 250 100 100 100 100 100 — 90 50 — 70 100 100 752-130 63 100 100 80 100 100 — 60 50 — 30 80 10 20 250 100 100 70 100 100— 70 60 — 50 90 30 25 2-131 63 100 100 80 100 100 — 70 30 — 30 90 15 10250 100 100 100 100 100 — 90 60 — 70 100 70 75 2-132 63 100 100 100 100100 — 40 20 — 10 80 60 50 250 100 100 99 100 100 — 60 40 — 25 100 75 802-133 63 100 100 80 90 100 — 70 50 — 30 100 70 75 250 100 100 100 100100 — 75 85 — 70 95 95 95 2-134 63 100 100 90 100 100 — 20 10 10 0 70 1050 250 100 100 100 100 100 — 60 30 30 30 90 20 80 2-135 63 100 100 70100 100 — 15 0 — 0 50 10 20 250 100 100 100 95 100 — 40 20 — 10 90 25 402-136 3 100 100 60 80 95 — 20 0 — 0 70 15 5 250 100 100 100 100 100 100— 30 10 — 20 90 10 10 2-137 63 100 100 100 100 100 — 10 0 — 0 70 10 10250 100 100 90 90 100 — 30 30 — 10 90 60 70 2-140 63 100 100 100 100 100— 40 30 — 20 100 10 50 250 100 100 100 100 100 — 60 85 — 65 100 70 802-141 63 95 100 50 100 95 — 20 10 — 10 70 5 15 250 95 100 95 95 100 — 4030 — 30 70 5 15 2-142 63 0 0 0 0 20 — 0 0 — 0 15 10 10 250 40 40 10 5060 — 0 0 — 0 30 15 0 2-143 63 100 100 70 60 — — 0 0 — 0 100 10 40 250100 100 100 100 — — 40 30 — 40 95 35 70 2-143 63 100 100 70 60 — 250 100100 100 100 — — 40 30 — 40 95 35 70 2-144 63 75 85 60 60 — — 0 0 — 0 4040 15 250 90 100 85 70 — — 30 10 — 0 40 20 35 2-145 63 95 100 100 100 —— 0 0 0 0 80 10 35 250 100 100 100 100 — — 40 20 10 10 95 20 60 2-146 6330 70 20 40 30 — 0 0 0 0 10 10 10 250 30 75 50 50 40 — 0 0 0 0 10 5 102-147 63 100 100 80 100 100 95 20 10 — 20 90 15 50 250 100 100 95 100100 100 40 50 — 50 100 90 75 2-148 63 100 100 95 80 100 — 50 50 0 40 8025 0 250 90 100 100 90 100 — 40 20 10 40 90 30 10 2-149 63 80 100 95 7090 — 10 20 0 0 80 0 0 250 80 100 95 95 95 — 20 50 0 20 90 15 10 2-151 6310 0 10 30 10 20 0 0 0 0 0 0 0 250 20 50 50 100 10 30 0 0 0 0 0 0 102-152 63 100 100 100 100 98 — 30 30 20 20 60 15 40 250 100 100 100 100100 — 50 50 40 30 70 30 65 2-153 63 60 95 0 100 80 — 20 10 0 0 70 5 0250 90 100 30 95 95 — 30 20 20 10 50 5 10 2-154 63 100 100 50 100 100 —40 80 — 10 90 10 65 250 100 100 100 100 100 — 95 95 — 85 100 85 90 2-15563 100 100 100 100 100 — 50 30 30 40 80 70 25 125 100 100 100 100 100 —70 60 50 50 99 90 80 2-158 63 100 95 90 20 90 50 10 0 0 0 40 0 20 250100 100 100 80 95 100 70 50 0 30 50 0 60 2-161 63 100 100 100 100 100 300 20 0 0 80 0 20 250 100 100 100 100 100 100 20 60 30 50 80 20 70 2-16363 100 99 90 98 100 — 50 55 0 30 80 35 20 250 100 100 90 95 100 — 60 7010 45 85 40 55 2-168 63 20 60 0 60 30 — 0 0 0 0 30 5 10 250 50 100 80100 50 — 10 0 0 0 80 10 30 2-169 63 10 70 10 50 30 — 0 0 0 0 70 10 10250 0 80 10 40 40 — 0 0 0 0 50 10 10 2-170 63 20 35 10 50 60 — 10 0 0 030 5 5 250 30 90 60 95 50 — 20 20 10 30 90 15 10 2-171 63 30 60 30 60 40— 0 0 0 0 20 0 0 250 50 100 40 100 90 — 10 0 10 10 80 10 10 2-172 63 6060 50 90 35 30 0 0 0 0 20 5 0 250 60 100 90 100 60 80 10 0 0 0 80 10 102-173 63 50 60 50 100 40 30 0 0 0 0 20 0 0 250 50 100 70 80 65 50 0 0 00 40 5 10 2-174 63 60 60 60 70 55 — 10 0 0 0 30 10 20 250 60 80 75 80 85— 10 0 0 10 80 25 20 2-175 63 100 100 100 100 100 — 0 0 0 0 80 10 50 250100 100 100 100 100 — 20 20 10 10 90 10 80 2-176 63 100 50 10 70 80 — 00 0 0 15 0 10 250 100 90 30 95 90 — 0 0 0 0 35 5 30 2-177 63 100 100 100100 100 — 45 20 30 30 95 15 50 250 100 100 100 100 100 — 60 40 40 50 10020 60 2-178 63 50 40 0 30 30 — 0 0 0 0 10 0 0 250 70 50 0 20 40 — 0 0 00 15 0 0 2-179 63 100 100 80 80 80 — 30 70 10 0 90 15 30 250 100 100 100100 100 — 55 50 50 — 100 15 60 2-180 63 100 100 100 100 100 — 60 40 — 40100 5 20 250 100 100 100 100 100 — 70 60 — 40 100 20 65 2-181 63 100 100160 100 100 — 70 40 — 30 90 10 15 250 100 100 100 100 100 — 80 60 — 7095 20 60 2-182 63 90 100 60 100 95 — 10 0 — 0 70 5 0 250 95 100 95 100100 — 80 30 — 20 100 70 2-183 63 0 0 0 0 0 — 0 0 — 0 10 0 0 250 10 50 040 80 — 0 0 — 0 30 0 0 2-184 63 100 100 100 100 100 — 60 40 — 20 95 1040 250 100 100 100 100 100 — 80 50 — 90 100 75 65 2-185 63 80 100 40 6070 — 0 0 — 0 50 0 20 250 100 100 60 80 100 — 20 0 — 10 75 5 35 2-187 6399 100 70 100 100 — 40 20 — 10 100 15 50 250 100 100 100 100 100 — 60 40— 40 100 75 90 2-188 63 85 100 55 100 80 — 10 30 — 0 70 25 20 250 90 10090 100 100 — 20 40 — 10 95 45 40 2-189 40.5 100 85 40 60 100 — 0 0 0 015 0 0 162 100 100 60 100 100 — 0 10 0 0 60 5 5 2-190 63 95 90 20 50 90— 0 0 0 0 20 5 0 250 99 90 80 90 100 — 0 10 50 0 95 10 5 2-191 63 40 7030 80 — — 0 0 0 0 20 10 10 250 90 90 80 100 — — 10 0 0 0 35 20 20 2-19263 70 85 40 50 60 — 0 0 0 0 40 5 0 250 70 85 60 70 50 — 0 0 0 0 70 15 202-194 63 99 95 50 95 90 95 20 0 0 0 50 5 30 250 99 100 70 99 100 90 2010 10 20 95 5 40 2-196 63 100 100 100 90 100 100 30 10 10 10 100 10 30250 100 100 100 100 100 90 20 10 10 20 — 15 — 2-197 63 100 100 80 100100 — 10 0 0 10 70 10 20 250 100 100 80 90 100 — 20 20 50 10 100 10 302-198 63 80 80 50 80 80 — 10 5 0 10 90 10 10 250 95 100 30 100 90 — 10 550 10 95 40 30 2-199 63 95 100 100 100 100 — 50 60 40 30 90 30 80 250100 100 100 100 100 — 90 100 95 95 100 90 90 2-200 63 100 100 100 100100 — 30 0 0 0 80 10 10 250 100 100 100 100 100 — 50 0 0 0 95 20 202-201 63 99 95 60 95 95 — 20 50 0 35 75 30 60 250 100 99 85 95 98 — 3060 0 45 85 35 65 2-202 63 100 100 100 100 100 — 30 10 — 0 90 15 20 250100 100 100 100 100 — 40 40 — 30 100 30 60 2-203 63 100 100 100 60 100 —20 10 10 10 30 10 25 250 100 100 100 95 100 — 30 30 20 30 60 10 30 2-20463 50 40 10 30 20 10 0 0 0 0 30 5 0 250 70 80 500 60 95 70 20 0 0 10 8010 30 2-205 63 90 100 90 100 70 70 10 0 0 10 40 10 30 250 40 100 100 7070 100 10 0 0 10 30 20 30 2-206 63 20 50 50 70 50 — 0 0 0 30 30 0 0 25050 90 80 90 70 — 0 30 0 20 70 0 70 3-1 63 0 0 0 0 0 0 0 0 0 0 0 0 0 25060 0 0 30 60 0 0 0 0 0 0 10 0 3-4 63 0 40 0 0 0 — 0 0 0 0 10 0 0 250 050 0 0 0 — 0 0 0 0 20 0 10 3-6 63 100 100 40 90 50 — 0 0 0 0 95 20 30250 100 100 90 100 90 — 40 20 20 10 100 70 70 3-26 63 50 60 20 60 50 — 00 0 0 15 3 10 250 65 60 60 90 60 — 0 0 0 0 30 10 30 4-1 63 50 100 30 10060 40 0 0 0 0 50 10 30 250 95 100 50 100 98 90 10 0 20 0 100 20 50 4-263 50 70 0 70 40 0 0 0 0 0 40 0 0 250 85 100 40 100 95 30 20 0 0 0 75 1030 4-23 63 100 100 80 100 80 — 40 20 10 10 95 35 60 250 100 100 100 100100 — 70 60 50 40 100 80 80 4-24 63 100 100 70 100 100 — 50 — 40 40 8035 20 250 100 100 100 100 100 — 80 — 60 50 95 70 45 4-26 63 100 100 30100 90 — 20 10 10 20 40 5 15 250 100 100 60 100 100 — 60 50 50 50 80 2045 4-27 63 60 70 20 70 60 — 0 0 0 0 30 5 0 250 80 100 40 80 100 — 10 0 00 50 10 10 4-28 63 80 100 50 60 70 — 10 0 0 0 40 0 10 250 100 100 50 8090 — 30 20 10 20 50 5 15 4-29 63 100 100 90 100 90 — 80 70 60 50 100 9080 250 100 100 100 100 100 — 99 90 100 90 100 100 85 4-30 63 100 100 100100 100 — 80 50 50 50 100 90 80 250 100 100 100 100 100 — 100 90 100 85100 99 85 4-31 63 100 100 10 100 100 — 20 10 0 0 40 10 20 250 100 100 30100 100 — 40 10 10 10 80 25 40 4-32 63 100 90 80 100 100 — 30 0 10 10 5020 20 250 100 100 80 100 100 — 50 20 30 20 80 30 40 4-33 63 100 100 30100 90 — 30 10 0 10 70 15 30 250 100 100 70 100 100 — 40 20 30 30 80 2540 4-34 63 100 100 90 100 100 — 50 20 30 35 90 25 40 250 100 100 100 10090 — 75 50 30 60 95 50 80 4-36 63 100 100 100 100 100 — 90 20 10 30 10050 60 250 100 100 100 100 100 — 90 60 90 70 100 100 100 4-37 63 100 10090 100 100 — 90 20 40 50 80 20 10 250 100 100 100 100 100 — 90 60 60 70100 60 60 4-38 63 100 100 90 100 100 — 60 50 — 40 80 40 35 250 100 100100 100 100 — 80 50 — 40 100 85 50 4-39 63 100 100 100 100 100 — 80 60 —50 100 70 60 250 100 100 100 100 100 — 90 90 — 80 100 100 60 4-40 63 100100 100 100 100 — 80 50 — 40 90 30 40 250 100 100 100 100 100 — 90 90 —90 100 75 50 4-41 63 100 100 100 100 100 — 95 80 — 90 100 75 50 250 100100 100 100 100 — 95 90 — 100 100 90 85 4-42 63 75 100 0 40 80 — 0 0 — 020 0 0 250 100 100 0 30 90 — 0 10 — 0 40 0 0 4-43 63 70 60 50 40 80 — 00 — 0 30 0 0 250 100 100 60 40 90 — 40 10 — 0 40 10 0 4-44 63 100 100100 100 100 — 95 70 — 70 100 90 70 250 95 100 100 100 100 — 90 90 — 95100 100 80 4-45 63 90 100 80 95 100 — 30 20 — 10 30 10 10 250 95 100 80100 100 — 60 20 — 20 80 20 20 4-46 63 100 95 80 100 90 — 10 20 — 0 50 1010 250 100 90 95 80 100 — 10 30 — 20 100 80 70 4-47 63 75 100 100 85 100— 40 30 — 40 90 30 30 250 95 10 100 100 100 — 60 50 — 30 95 65 60 4-4863 100 100 95 100 100 — 30 20 — 20 95 90 80 250 100 100 100 100 100 — 4080 — 40 100 90 80 4-49 63 100 100 80 80 100 — 30 10 0 10 40 20 10 250100 100 100 100 100 — 30 10 10 10 90 80 70 4-50 63 30 60 0 30 40 — 0 0 00 15 0 0 250 70 95 20 90 95 — 0 0 0 0 20 10 0 4-53 63 70 100 30 100 60 —10 0 0 0 60 5 30 250 100 100 90 100 90 — 70 60 40 40 90 70 65 4-54 63100 100 90 100 100 — 80 70 40 30 70 40 90 250 100 100 100 100 100 — 9080 40 30 70 75 100 4-55 63 50 100 20 40 50 — 10 0 0 0 30 10 0 250 80 10040 85 90 — 40 20 10 10 60 5 30 4-56 63 100 100 100 100 100 — 90 50 40 20100 80 65 250 100 100 100 100 100 — 100 90 90 70 100 100 85 4-57 63 100100 60 100 95 — 50 30 30 10 95 40 50 250 100 100 100 100 100 — 90 40 5060 100 90 80 4-58 63 100 100 90 100 100 — 50 30 30 20 100 30 60 250 100100 100 100 100 — 90 40 50 60 100 70 75 4-59 63 90 100 30 100 90 — 0 0 00 60 5 50 250 100 100 60 100 100 — 30 20 30 20 90 25 60 4-60 63 100 10060 100 100 — 65 60 50 40 90 25 50 250 100 100 100 100 100 — 90 50 50 60100 55 70 4-61 63 100 100 100 100 100 — 70 40 50 60 100 50 40 250 100100 100 100 100 — 80 60 70 70 95 70 80 4-62 63 100 100 90 100 100 — 6020 30 10 100 30 30 250 100 100 100 100 100 — 80 40 30 50 90 45 30 4-6363 100 100 100 100 100 — 0 0 0 0 90 10 10 250 100 100 100 100 100 — 3020 10 10 100 30 60 4-64 63 100 100 60 100 100 — 50 20 10 10 100 30 15250 100 100 100 100 100 — 80 30 30 30 90 40 50 4-65 63 100 100 100 100100 — 100 60 70 60 100 80 70 250 100 100 100 100 100 — 100 70 80 80 10090 80 4-66 63 80 100 20 100 80 — 10 0 0 10 40 15 30 250 100 100 90 100100 — 60 40 50 50 80 60 70 4-67 63 100 100 100 100 100 — 90 40 — 70 10055 50 250 100 100 100 100 100 — 90 70 — 80 100 70 70 4-68 63 100 100 100100 100 — 100 90 — 75 100 95 60 250 100 100 100 100 100 — 100 98 — 90100 100 80 4-69 63 100 100 40 70 90 — 40 20 — 20 40 5 0 250 100 100 70100 100 — 80 40 — 50 80 35 40 4-70 63 90 100 60 100 90 — 60 40 — 30 10040 70 250 100 100 90 100 100 — 95 80 — 70 100 90 10 5-17 63 0 90 0 30 20— 0 0 0 0 15 0 10 250 30 100 30 40 60 — 80 20 10 0 70 10 50 5-18 63 0 700 0 10 — 0 0 0 0 10 0 20 250 10 70 0 0 10 — 0 0 0 0 20 10 20 5-26 63 100100 90 90 100 — 40 20 — 20 70 10 50 250 90 100 100 70 100 — 70 60 — 3080 15 60 5-28 63 100 100 90 100 100 — 10 0 — 10 60 25 60 250 100 100 100100 100 — 30 50 — 30 90 70 70 6-13 63 70 100 0 50 85 — 60 0 0 20 30 1510 250 90 90 30 60 90 — 90 30 10 30 45 20 30 6-14 63 80 100 60 100 100 —90 20 30 60 100 60 60 250 100 100 90 100 100 — 100 90 90 90 100 100 906-15 63 100 100 100 100 100 — 50 40 — 30 90 15 60 250 100 100 100 100100 — 85 70 — 60 90 25 90 6-16 63 100 100 80 100 100 — 30 20 — 20 40 2020 250 90 100 60 75 100 — 60 40 — 30 70 35 70 6-17 63 90 60 50 50 90 — 00 — 0 20 5 0 250 70 100 70 70 90 — 30 30 — 20 20 15 10 6-19 63 0 0 0 0 0— 0 0 0 0 0 0 0 250 30 50 0 30 60 — 0 0 0 0 10 0 0 6-20 63 0 0 0 0 0 — 00 0 0 0 0 0 250 60 50 0 40 60 — 0 0 0 0 10 0 0 6-22 63 70 60 0 20 50 — 00 0 0 30 0 0 250 100 80 0 70 70 — 0 0 0 0 30 0 30 6-23 63 20 40 0 10 20— 0 0 0 10 0 0 0 250 85 55 10 30 70 — 30 0 0 10 30 15 15 6-24 63 0 20 00 30 — 0 0 0 0 10 0 0 250 88 95 10 60 90 — 40 0 0 0 20 0 0 7-2 63 100100 — 80 95 0 20 30 20 20 40 10 30 250 100 100 — 100 100 10 50 90 40 7080 10 20 7-14 63 — — — — — — — — — — — — — 250 70 95 60 100 90 — 20 10 —10 40 25 15 8-2 63 95 100 50 50 40 30 40 20 10 30 40 10 20 250 100 10030 90 80 90 60 30 0 30 80 20 15 8-3 63 90 90 0 40 70 — 0 0 0 0 20 0 20250 100 100 50 60 90 — 70 0 20 0 30 0 80 8-4 63 70 60 0 0 70 — 0 0 0 030 0 50 250 90 80 10 20 90 — 30 0 0 0 50 0 50 8-5 63 40 70 0 0 70 — 0 00 0 20 0 40 250 100 90 10 40 70 — 20 0 0 0 50 0 50 8-7 63 95 95 0 10 95— 0 0 0 0 50 10 0 250 100 100 90 70 99 — 90 20 0 10 90 10 90 8-13 63 100100 30 50 90 — 30 20 10 20 30 10 30 125 100 100 50 60 90 — 30 40 20 1060 40 70 8-18 63 100 100 30 50 70 — 30 10 10 10 30 5 50 250 100 100 4060 80 — 30 30 3020 70 30 60 8-30 63 100 100 80 100 100 — 40 30 30 20 9010 40 250 100 100 100 100 100 — 70 70 50 40 95 15 35 8-31 63 100 100 60100 100 — 20 — 10 10 80 10 45 250 100 100 80 100 100 — 20 — 30 30 90 1030 8-36 63 95 100 70 100 95 — 10 0 0 10 30 10 10 250 90 100 95 85 100 —10 20 10 5 40 15 20 9 4 63 50 50 20 45 70 — 20 — 0 0 40 5 10 250 80 10060 100 85 — 30 — 10 0 90 10 40 9-14 63 85 100 40 80 95 — 10 0 — 0 60 150 250 100 100 40 90 100 — 20 10 — 10 90 50 40 9-15 63 100 100 100 100100 — 10 0 0 0 100 5 40 250 100 100 100 100 100 — 35 10 10 20 100 10 709-16 63 30 100 50 90 65 — 0 0 0 10 90 5 30 250 75 100 85 100 80 — 20 100 0 100 65 70 9-19 63 80 100 80 75 100 — 10 0 0 0 60 10 15 250 98 100 9590 100 — 20 10 0 10 80 10 25 11-6 63 100 100 100 70 80 100 10 50 0 0 100 20 250 100 100 100 100 100 100 50 80 0 0 40 20 60 11-13 63 100 95 8598 100 — 55 65 0 40 65 45 45 250 100 100 85 98 100 — 40 55 15 60 85 4565 12-2 63 30 100 50 90 100 — 0 30 10 0 60 10 20 250 100 100 95 100 100— 50 80 90 70 100 100 80 12-3 63 95 90 20 50 90 — 0 0 0 0 20 5 0 250 9990 80 90 100 — 0 10 50 0 95 10 5 12-5 63 70 100 40 100 100 — 20 10 — 040 25 20 250 85 100 60 99 99 — 10 10 — 10 30 20 15 12-8 63 80 100 50 9095 — 20 10 0 10 40 5 20 250 90 100 70 80 99 — 25 10 10 0 80 10 15 13-363 90 100 90 75 100 — 10 0 — 0 30 10 25 250 90 90 100 70 100 — 30 20 —10 40 10 20 13-4 63 100 100 95 85 95 — 20 10 — 0 70 5 30 250 95 100 10085 100 — 40 30 — 10 90 5 50 13-5 63 70 70 40 50 95 — 0 0 0 0 10 7 10 25075 70 30 60 90 — 10 0 0 20 25 15 20 14-1 63 100 85 55 85 80 — 40 85 2580 100 85 40 250 100 98 70 100 98 — 70 95 75 95 100 100 80 14-2 63 10080 50 75 95 — 30 0 0 20 35 35 25 250 100 100 60 100 95 — 20 45 30 40 4045 30 14-3 63 95 100 10 50 90 — 30 99 80 99 100 100 5 250 100 100 75 100100 — 70 100 70 100 100 100 80 14-4 63 100 80 50 50 100 — 30 85 — 75 10070 15 250 100 100 100 60 100 — 65 99 — 95 100 80 40 14-5 63 100 100 1030 100 — 60 40 — 95 20 70 20 250 100 100 50 100 100 — 95 100 — 100 95100 30 14-6 63 95 90 50 70 80 40 30 99 50 50 100 50 0 250 100 100 100100 100 80 80 100 65 75 100 60 35 14-7 63 95 50 0 20 90 50 60 100 70 8085 95 10 250 100 100 20 60 99 90 85 100 90 100 99 100 25 14-8 63 90 6030 30 70 10 10 95 — 40 95 40 5 250 100 100 80 95 99 50 40 99 — 85 100 8030 14-10 63 90 70 0 0 60 10 30 98 — 75 80 70 5 250 100 100 90 80 100 —90 100 50 100 100 60 20 14-11 63 95 80 50 90 50 — 80 100 80 99 60 100 10250 100 100 80 100 100 — 100 100 9 100 100 60 20 14-12 63 85 10 20 40 9080 30 98 — 50 95 30 0 250 90 85 80 70 99 80 40 99 — 60 100 85 10 14-1363 90 30 0 40 60 30 20 100 — 65 75 55 0 250 100 80 20 60 100 40 40 99 —90 98 100 15 14-14 63 50 50 0 30 50 70 50 100 0 90 100 10 0 250 100 10060 50 90 70 70 100 20 100 100 50 30 14-15 63 100 60 0 50 50 20 70 100 5095 40 20 0 250 100 90 50 90 100 100 80 100 40 100 100 60 0 14-16 63 6060 20 40 95 — 0 95 0 95 100 0 0 250 100 100 40 50 100 — 30 100 30 100100 70 10 14-17 63 100 100 20 20 90 — 20 100 50 100 80 70 0 250 100 10030 70 100 — 70 100 90 100 100 95 0 14-18 63 100 30 20 30 99 0 10 99 1020 10 20 10 250 100 60 60 60 100 10 20 100 30 60 40 50 25 14-19 63 90 6040 30 90 — 0 100 0 100 100 0 0 250 100 100 70 90 100 — 30 100 0 100 10040 20 14-20 63 95 99 0 50 80 — 0 100 10 100 70 0 0 250 100 100 50 70 100— 50 100 90 100 100 80 10 14-21 63 90 100 30 40 70 50 10 99 10 70 95 5010 250 100 95 60 50 95 95 40 100 70 98 10 100 45 14-22 63 50 30 0 10 50100 30 100 40 80 95 10 0 250 100 100 50 80 90 100 60 100 60 95 100 50 1014-23 63 50 50 20 80 50 50 60 100 40 50 100 0 0 250 100 90 70 95 80 4070 100 50 95 100 40 20 14-24 63 40 70 0 20 80 50 0 100 0 95 30 10 10 25090 100 0 40 90 50 50 100 50 100 100 20 50 14-25 63 95 100 50 70 80 10050 100 40 95 100 100 10 250 100 100 80 100 100 100 80 100 95 100 100 10050 14-26 63 90 70 50 20 60 100 0 100 30 100 100 40 10 250 100 100 90 100100 100 0 100 70 100 100 100 10 14-27 63 50 70 50 70 90 — 0 99 0 70 95 50 250 90 80 30 50 100 — 20 100 10 95 100 10 0 14-28 63 90 100 20 50 95 —0 100 0 20 80 10 0 250 100 100 30 70 100 — 30 100 50 50 100 70 40 14-2963 90 50 0 80 30 100 20 100 50 70 100 15 0 250 100 100 40 80 60 100 70100 70 95 100 50 10 14-30 63 70 60 20 0 50 — 0 100 0 60 100 10 0 250 100100 60 50 100 — 30 100 50 100 100 20 0 14-31 63 90 90 50 10 70 — 0 100 095 50 10 0 250 100 100 50 70 90 — 50 100 20 100 100 50 0 14-32 63 95 9020 0 0 40 40 100 0 70 70 0 0 250 100 95 40 20 80 40 70 100 10 90 100 0 014-33 63 100 90 0 20 20 0 40 100 10 70 10 10 0 250 100 100 0 20 70 10090 100 95 100 70 95 0 14-34 63 100 99 40 60 100 40 100 100 60 70 99 8025 250 100 100 100 90 100 100 100 100 80 99 100 100 70 14-35 63 100 95 070 100 100 50 100 30 50 100 100 80 250 100 100 90 100 100 100 95 100 7095 100 100 100 14-36 63 100 95 20 30 99 100 85 99 20 40 95 95 35 250 100100 40 70 100 95 99 100 40 65 100 95 60 14-37 63 100 100 20 30 100 10090 100 0 80 90 20 70 250 100 100 50 100 100 100 100 100 30 100 100 95100 14-38 63 100 100 0 70 100 — 90 100 0 95 0 50 0 250 100 100 0 70 100— 100 100 30 100 20 100 40 14-39 63 100 99 60 20 100 50 95 100 30 60 9030 90 250 100 100 100 50 100 50 100 100 40 100 100 50 100 14-40 63 10090 20 30 100 90 85 100 20 20 50 35 15 250 100 100 60 60 100 100 99 10020 40 95 70 75 14-41 63 100 100 0 30 100 — 90 100 40 100 100 100 20 250100 100 0 50 100 — 100 100 70 100 100 100 95 14-42 63 100 100 60 100 100— 100 100 60 95 100 100 95 250 100 100 90 100 100 — 100 100 95 100 100100 100 14-43 63 100 100 40 95 100 — 90 100 80 80 100 95 95 250 100 10090 100 100 — 100 100 95 100 100 100 100 14-44 63 100 100 0 50 100 — 100100 30 100 100 100 90 250 100 100 0 90 100 — 100 100 80 100 100 100 10014-45 63 100 100 30 100 100 100 70 100 70 90 90 70 70 250 100 100 30 100100 100 95 100 90 100 100 100 100 14-46 63 95 100 60 100 100 — 90 100 8080 100 95 60 250 100 100 90 100 100 — 100 100 95 100 100 100 100 14-4763 100 100 0 80 100 100 90 100 70 95 100 40 100 250 100 100 70 100 100100 100 100 80 100 100 100 100 14-48 63 100 100 0 0 100 80 50 50 0 70 9540 70 250 100 100 100 100 100 — 100 100 90 90 100 100 100 14-49 63 100100 70 100 100 100 80 100 70 70 95 80 50 250 100 100 95 100 100 100 100100 95 95 100 100 95 14-50 63 100 30 90 0 50 — 0 0 0 0 0 10 30 250 10050 100 0 100 — 0 0 0 50 20 30 50 14-51 63 0 0 0 0 0 0 0 10 0 0 0 0 0 2500 50 0 30 10 20 0 20 0 0 30 0 0 14-52 63 20 90 0 100 — — 0 0 0 0 0 0 0250 50 100 70 100 — — 0 10 0 0 100 10 0 14-54 63 40 60 0 30 20 — 10 30 00 30 5 10 250 50 80 30 80 60 — 10 30 0 10 35 15 10 14-55 63 30 70 10 7030 — 0 10 0 0 10 5 20 250 — — — — — — — — — — — — — 14-56 63 100 70 30100 99 90 30 20 30 10 40 10 0 250 100 100 40 100 100 80 70 80 70 50 5030 25 14-59 63 20 50 0 30 10 — 0 0 0 0 0 0 0 250 20 30 10 30 10 — 0 0 00 10 0 0 14-60 63 70 100 40 100 99 — 20 50 20 10 100 10 10 250 100 10070 100 100 — 30 75 50 60 100 60 20 14-61 63 20 30 0 20 40 — 0 0 0 0 0 00 250 60 60 30 50 75 — 20 60 20 70 40 70 30 14-62 63 30 40 0 30 10 40 00 — 0 15 5 0 250 50 60 30 50 20 30 0 0 — 0 15 5 5 14-63 63 95 90 95 7080 20 50 100 — 40 95 35 5 250 100 100 100 70 100 50 70 99 — 90 100 80 1514-64 63 100 100 10 30 70 30 30 100 — 40 80 99 5 250 100 100 20 80 99 4070 100 — 99 90 100 10 14-65 63 100 100 90 50 90 — 100 100 30 99 100 0 0250 100 100 100 70 100 — 100 100 50 100 100 50 10 14-66 63 95 100 80 7080 — 95 100 60 100 80 90 0 250 100 100 90 90 99 — 100 100 80 100 99 10010 15-1 63 100 100 100 100 100 — 80 80 — 90 100 80 75 250 100 100 100100 100 — 100 99 — 100 100 95 95 15-2 63 20 80 10 90 — — 0 0 0 0 40 1550 250 95 100 75 100 — — 80 90 70 80 100 80 75 15-3 63 95 100 70 95 95 —30 10 0 20 90 25 50 250 100 100 100 100 100 — 80 90 90 80 100 80 90 15-463 70 100 80 100 100 — 50 40 — 30 90 50 70 250 100 100 80 100 100 — 8090 — 70 100 90 95 15-5 63 70 100 40 90 100 — 70 70 — 30 100 70 60 250100 100 80 100 100 — 80 90 — 70 100 90 90 15-6 63 50 100 30 50 — — 30 20— 0 60 25 60 250 85 100 70 100 — — 75 95 — 90 100 80 95 15-7 63 100 10060 100 100 — 30 40 — 20 90 60 50 250 100 100 100 100 100 — 90 95 — 75100 80 90 15-8 63 20 70 0 50 95 — 0 0 — 0 60 0 10 250 60 100 40 90 90 —30 20 — 0 90 55 60 15-9 63 10 80 10 100 — — 0 0 — 0 40 30 50 250 95 10060 85 — — 80 90 — 80 95 70 90 15-10 63 100 100 100 100 100 — 30 10 30 6095 45 50 250 100 100 100 100 100 — 75 80 70 90 95 65 80 15-11 63 95 10090 100 100 — 40 50 50 50 95 45 65 250 100 100 100 100 100 — 80 99 99 95100 85 99 15-12 63 95 100 90 100 100 — 70 70 80 95 100 80 80 250 100 100100 100 100 — 100 100 99 100 100 95 99 15-13 63 80 100 60 100 95 — 20 2010 10 95 15 60 250 95 100 100 100 100 — 60 85 70 70 100 50 90 15-14 63100 100 80 100 100 — 20 20 20 20 100 20 40 250 100 100 100 100 100 — 5590 70 60 100 65 50 15-15 63 100 100 80 90 100 — 40 30 30 40 95 45 70 250100 100 100 100 100 — 95 100 99 100 100 90 95 15-16 63 80 100 80 100 100— 30 10 10 20 95 15 70 250 100 100 100 100 100 — 60 90 70 80 100 45 8015-17 63 90 100 80 100 — — 40 50 20 40 90 35 75 250 100 100 100 100 — —90 99 95 99 100 80 90 15-18 63 100 100 40 90 100 — 20 10 0 10 90 20 30250 100 100 100 100 100 — 80 95 99 100 100 80 85 15-19 63 100 100 75 100100 — 40 50 40 50 90 35 65 250 100 100 100 100 100 — 100 100 100 100 10085 90 15-20 63 100 100 80 100 100 — 80 50 — 30 95 40 35 250 100 100 100100 100 — 100 100 — 90 100 85 80 15-21 63 95 100 100 100 100 — 50 60 4030 90 30 80 250 100 100 100 100 100 — 90 100 95 95 100 90 90 15-22 63100 100 70 100 100 — 40 40 — 30 90 30 50 250 100 100 100 100 100 — 95100 — 90 100 90 90 16-2 63 60 40 0 0 30 — 0 0 0 0 10 0 0 250 60 70 10 070 — 0 0 0 0 40 10 20 16-4 63 0 0 0 0 0 — 0 0 0 0 0 0 0 250 0 0 0 0 0 —0 0 0 0 0 0 0 16-6 63 70 70 0 30 0 — 0 0 20 20 0 0 0 250 70 100 0 70 70— 0 0 40 80 0 0 10 16-7 63 0 0 0 0 0 — 0 0 0 0 0 0 0 250 0 0 30 30 0 — 00 0 0 0 0 0 17-1 63 10 70 20 80 30 — 0 0 0 0 10 0 0 250 30 70 10 80 60 —0 0 0 0 30 0 0 17-2 63 0 0 0 0 0 — 0 0 0 0 0 0 0 250 30 50 10 20 40 — 00 0 0 10 0 0 17-4 63 20 35 10 40 20 — 0 0 0 0 10 0 0 250 70 70 20 80 40— 0 0 0 0 15 0 0 17-5 63 10 50 10 30 40 — 0 0 0 0 20 0 0 250 40 80 20 7080 — 0 0 0 0 35 10 0

1. A compound represented by the formula I or its salts

wherein X is hydrogen, halogen, nitro, amino, NHR, N(R)₂, amide,thioamide, cyano, alkylcarbonyl, alkoxycarbonyl, alkylsulfonamide,unsubstituted or substituted alkyl, haloalkyl, alkoxy, haloalkoxy,alkoxycarbonylalkoxy, benzyloxy, aryloxy, or heteroaryloxy; Y ishydrogen, halogen, or nitro; W is hydrogen, OR, SR, NHR, N(R)₂, CH₂R,CH(R)₂, C(R)₃, halogen, nitro, or cyano, where multiple R groupsrepresent any possible combination of substituents described by R; R ishydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, alkoxy,cycloalkyloxy, aryloxy, heteroaryloxy, alkylsulfonyl, benzyl,alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl,heteroarylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, orheteroaryloxycarbonyl, where any of these groups may be unsubstituted orsubstituted with any of the functional groups represented by one or moreof the following: halogen, cyano, nitro, amino, carboxyl, alkyl,haloalkyl, alkylsilyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy,alkoxycarbonyl, haloalkoxy, haloalkoxycarbonyl, alkylsulfonyl,haloalkylsulfonyl, aryl, heteroaryl, or cycloalkyl; Q is a heterocycle,examples of which are as follows:

wherein R₁ is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, amino,alkoxyalkyl, acetyl, alkoxycarbonylamino, alkylcarbonylamino, oralkoxycarbonyl; R₂ is alkyl or haloalkyl; R₁ and R₂ could combine toform a five- or six-membered heterocyclic ring; R₃ is hydrogen, halogen,nitro, amino, alkylamino, haloalkylamino, cyano, or amide; R₈ and R₉ areindependently oxygen, sulfur, or imino group; Q6, Q7, and Q10 mayoptionally be unsaturated containing one or two double bonds in the6-membered ring; Z is amino, hydroxyl, thiol, formyl, carboxyl, cyano,alkylcarbonyl, arylcarbonyl, azido, or one of the following:

wherein R₄ is alkyl, alkenyl, alkynyl, amino, cycloalkyl,heterocycloalkyl, alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl,alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl,arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, alkylthiocarbonyl,cycloalkyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl,aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl,alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl,alkoxycarbonylcarbonyl or arylcarbonylcarbonyl, where any of thesegroups may be unsubstituted or substituted with any of the functionalgroups represented by one or more of the following: halogen, cyano,nitro, amino, dialkylamino, hydroxyl, carboxyl, alkyl, alkenyl, alkynyl,cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy, alkoxycarbonyl,alkylthio, alkylthiocarbonyl, alkoxythiocarbonyl alkylamninocarbonyl,arylaminocarbonyl, alkylsulfonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, heteroaryl, heteroaryloxycarbonyl or methylenedioxy, whereinthe alkyl moiety or aryl moiety may be substituted with halogen, cyano,nitro, alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl,aryl, or heterocycloalkyl; and R₅ is hydrogen or any one of the groupsrepresented by R₄; or R₄ and R₅ could combine to form a 4-8 memberedheterocyclic ring;

wherein R₆ represents alkyl, haloalkyl, dialkylamino, unsubstituted orsubstituted aryl and heteroaryl; and R₇ represents hydrogen, halogen orany of the groups represented by R₆; —OR₄, —SR₄, —CH₂R₁₀, —CH(R₁₀)₂,—C(R₁₀)₃, or —CH═CHR₁₀ wherein R₁₀ is carboxyl, alkyl, alkenyl, alkynyl,amino, cycloalkyl, heterocycloalkyl, alkylsulfonyl, arylsulfonyl,benzyl, aryl, heteroaryl, alkylcarbonyl, alkenylcarbonyl,alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,alkoxycarbonyl, alkylthiocarbonyl, cycloalkyloxycarbonyl,aryloxycarbonyl, arylthio-carbonyl, aryl-thiocarbonyl,heteroaryloxycarbonyl, aminocarbonyl, alkylaminocarbonyl,arylaminocarbonyl, heteroarylaminocarbonyl, alkoxycarbonylcarbonyl orarylcarbonylcarbonyl, where any of these groups may be unsubstituted orsubstituted with any of the functional groups represented by one or moreof the following: halogen, cyano, nitro, amino, dialkylamino, hydroxyl,carboxyl, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcarbonyl,alkylcarbonyloxy, alkoxy, alkoxycarbonyl, alkylthio, alkylthiocarbonyl,alkoxythiocarbonyl alkylaminocarbonyl, arylaminocarbonyl, alkylsulfonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy,aryloxycarbonyl, arylthio, heteroaryl, heteroaryloxycarbonyl ormethylenedioxy, wherein the alkyl moiety or aryl moiety may besubstituted with halogen, cyano, nitro, alkyl, alkoxy, haloalkyl,haloalkoxy, alkoxycarbonyl, cycloalkyl, aryl, or heterocycloalkyl;provided that (1) Z is not alkyl, alkoxy, haloalkyl, haloalkoxy,alkylthio, haloalkylthio, alkenyl, haloalkenyl, amino, monoalkylamino,dialkylamino, alkoxyalkoxy or cyano, when Q is Q1 and R₂ is haloalkyl,(2) Z is not amino when Q is Q3, and (3) Z is not hydroxyl, alkoxy,alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy, or —NR₄R₅, whereinR₄ is alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl,alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, or cycloalkylalkyl, and R₅is alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl,alkylcarbonyl, alkoxycarbonyl, or cycloalkylalkyl, when Q is Q14 or Q15.2. The compound according to claim 1 wherein Z is represented by thefollowing:

wherein R₄ and R₅ are the same as defined in claim 1; or —CH₂R₁₀,wherein R₁₀ is the same as defined in claim
 1. 3. The compound accordingto claims 1 or 2 wherein X is halogen or cyano; Y is halogen; W is OR; Ris alkyl, alkenyl, or alkynyl, where any of these groups may beunsubstituted or substituted with any of the functional groupsrepresented by one or more of the following: halogen, cyano, nitro,amino, or carboxyl.
 4. The compound according to claim 1 wherein Q is

wherein R₁ is alkyl, amino, or haloalkyl; R₂ is haloalkyl; R₃ishydrogen; R₈ and R₉ are independently oxygen, sulfur, or imino group. 5.The compound according to claim 1 wherein X is halogen; Y is fluorine; Wis OR; R is alkyl, alkenyl, or alkynyl, where any of these groups may beunsubstituted or substituted with halogen or cyano; Q is

wherein R₁ is alkyl, amino, or haloalkyl; R₂is haloalkyl; R₃ ishydrogen; R₈ and R₉ are independently oxygen, sulfur, or imino group; Zis represented by the following:

wherein R₄ is alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl,alkylthiocarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl,arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl,aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl,heteroarylaminocarbonyl, alkoxycarbonylcarbonyl, orarylcarbonylcarbonyl, where any of these groups may be unsubstituted orsubstituted with any of the functional groups represented by one or moreof the following: halogen, cyano, nitro, amino, dialkylamino, hydroxyl,carboxyl, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcarbonyl,alkylcarbonyloxy, alkoxy, alkoxycarbonyl, alkylthio, alkylthiocarbonyl,alkoxythiocarbonyl alkylaminocarbonyl, arylamninocarbonyl,alkylsulfonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryl,arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, heteroaryl,heteroaryloxycarbonyl, or methylenedioxy, wherein the alkyl moiety oraryl moiety may be substituted with halogen, cyano, nitro, alkyl,alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl, aryl, orheterocycloalkyl; and R₅ is hydrogen; or —CH₂R₁₀, wherein R₁₀ iscarboxyl, alkyl, alkenyl, or alkynyl, where any of these groups may beunsubstituted or substituted with any of the functional groupsrepresented by one or more of the following: halogen, cyano, nitro,amino, dialkylamino, hydroxyl, carboxyl, alkyl, alkenyl, alkynyl,cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy, alkoxycarbonyl,alkylthio, alkylthiocarbonyl, alkoxythiocarbonyl alkylaminocarbonyl,arylaminocarbonyl, alkylsulfonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, heteroaryl, heteroaryloxycarbonyl, or methylenedioxy, whereinthe alkyl moiety or aryl moiety may be substituted with halogen, cyano,nitro, alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl,aryl, or heterocycloalkyl.
 6. A compound selected from the groupconsisting of3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneand3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-amino-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione.7. A herbicidal composition, characterized in that it contains at leastone compound according to claim 1 and an agricultural adjuvant.
 8. Amethod for controlling undesired vegetation which comprises applying toa locus to be protected a herbicidally effective amount of a compound ofclaim
 1. 9. The method of claim 8 wherein the locus to be protected is acereal crop field.
 10. The method of claim 9 wherein the compound ofclaim 1 is applied to soil as a preemergent herbicide.
 11. The method ofclaim 9 wherein the compound of claim 1 is applied to plant foliage. 12.A method to defoliate potato and cotton using a compound of claim
 1. 13.A process for preparing a compound represented by the formula I-1 or itssalts:

wherein X is hydrogen, halogen, nitro, amino, NHR, N(R)₂, amide,thioamide, cyano, alkylcarbonyl, alkoxycarbonyl, alkylsulfonamide,unsubstituted or substituted alkyl, haloalkyl, alkoxy, haloalkoxy,alkoxycarbonylalkoxy, benzyloxy, aryloxy, or heteroaryloxy; Y ishydrogen, halogen, or nitro; W is hydrogen, OR, SR, NHR, N(R)₂, CH₂R,CH(R)₂, C(R)₃, halogen, nitro, or cyano, where multiple R groupsrepresent any possible combination of substituents described by R; R ishydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, alkoxy,cycloalkyloxy, aryloxy, heteroaryloxy, alkylsulfonyl, benzyl,alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl,heteroarylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, orheteroaryloxycarbonyl, where any of these groups may be unsubstituted orsubstituted with any of the functional groups represented by one or moreof the following: halogen, cyano, nitro, amino, carboxyl, alkyl,haloalkyl, alkylsilyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy,alkoxycarbonyl, haloalkoxy, haloalkoxycarbonyl, alkylsulfonyl,haloalkylsulfonyl, aryl, heteroaryl, or cycloalkyl; Q is a heterocycle,examples of which are as follows:

wherein R₁ is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, amino,alkoxyalkyl, acetyl, alkoxycarbonylamino, alkylcarbonylamino, oralkoxycarbonyl; R₂ is alkyl or haloalkyl; R₁ and R₂ could combine toform a five- or six-membered heterocyclic ring; R₃ is hydrogen, halogen,nitro, amino, alkylamino, haloalkylamino, cyano, or amide; R₈ and R₉ areindependently oxygen, sulfur, or imino group; Q6, Q7, and Q10 mayoptionally be unsaturated containing one or two double bonds in the6-membered ring; Z′ is one of the following:

wherein R₄ is alkyl, alkenyl, alkynyl, amino, cycloalkyl,heterocycloalkyl, alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl,alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl,arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, alkylthiocarbonyl,cycloalkyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl,aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl,alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl,alkoxycarbonylcarbonyl, or arylcarbonylcarbonyl, where any of thesegroups may be unsubstituted or substituted with any of the functionalgroups represented by one or more of the following: halogen, cyano,nitro, amino, dialkylamino, hydroxyl, carboxyl, alkyl, alkenyl, alkynyl,cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy, alkoxycarbonyl,alkylthio, alkylthiocarbonyl, alkoxythiocarbonyl alkylaminocarbonyl,arylaminocarbonyl, alkylsulfonyl, alkenyloxycarbonyl,alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, heteroaryl, heteroaryloxycarbonyl, or methylenedioxy, whereinthe alkyl moiety or aryl moiety may be substituted with halogen, cyano,nitro, alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl,aryl, or heterocycloalkyl; and R₅ is hydrogen or any one of the groupsrepresented by R₄; or R₄ and R₅ could combine to form a 4-8 memberedheterocyclic ring;

wherein R₆ represents alkyl, haloalkyl, dialkylamino, unsubstituted orsubstituted aryl and heteroaryl; and R₇ represents hydrogen, halogen orany of the groups represented by R₆; —CH₂R₁₀, —CH(R₁₀)₂, —C(R₁₀)₃, or—CH═CHR₁₀ wherein R₁₀ is carboxyl, alkyl, alkenyl, alkynyl, amino,cycloalkyl, heterocycloalkyl, alkylsulfonyl, arylsulfonyl, benzyl, aryl,heteroaryl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl,alkylthiocarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl,arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl,aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl,heteroarylaminocarbonyl, alkoxycarbonylcarbonyl or arylcarbonylcarbonyl,where any of these groups may be unsubstituted or substituted with anyof the functional groups represented by one or more of the following:halogen, cyano, nitro, amino, dialkylamino, hydroxyl, carboxyl, alkyl,alkenyl, alkynyl, cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy,alkoxycarbonyl, alkylthio, alkylthiocarbonyl, alkoxythiocarbonylalkylaminocarbonyl, arylaminocarbonyl, alkylsulfonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy,aryloxycarbonyl, arylthio, heteroaryl, heteroaryloxycarbonyl ormethylenedioxy, wherein the alkyl moiety or aryl moiety may besubstituted with halogen, cyano, nitro, alkyl, alkoxy, haloalkyl,haloalkoxy, alkoxycarbonyl, cycloalkyl, aryl, or heterocycloalkyl;provided that (1) Z′ is not alkyl, haloalkyl, alkenyl, haloalkenyl,monoalkylamnino, or dialkylamino, when Q is Q1 and R₂ is haloalkyl, and(2) Z′ is not —NR₄R₅, wherein R₄ is alkyl, alkenyl, alkynyl, cycloalkyl,haloalkyl, haloalkenyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, orcycloalkylalkyl, and R₅ is alkyl, alkenyl, alkynyl, cycloalkyl,haloalkyl, haloalkenyl, alkylcarbonyl, alkoxycarbonyl, orcycloalkylalkyl, when Q is Q14 or Q15, which comprises of reacting acompound represented by the formula II:

with a compound selected from the group consisting of an alkyl halide,alkyl acid halide, aryl acid halide, alkyl acid anhydride, aryl acidanhydride, alkylhaloformate, alkyl isocyanate, aryl isocyanate, alkyldihalide, aliphatic aldehyde, aliphatic ketone, aromatic aldehyde, andaromatic ketone.
 14. A compound represented by the formula III:

wherein X is hydrogen, halogen, nitro, amino, NHR, N(R)₂, amide,thioamide, cyano, alkylcarbonyl, alkoxycarbonyl, alkylsulfonamide,unsubstituted or substituted alkyl, haloalkyl, alkoxy, haloalkoxy,alkoxycarbonylalkoxy, benzyloxy, aryloxy, or heteroaryloxy; Y ishydrogen, halogen, or nitro; W is hydrogen, OR, SR, NHR, N(R)₂, CH₂R,CH(R)₂, C(R)₃, halogen, nitro, or cyano, where multiple R groupsrepresent any possible combination of substituents described by R; R ishydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, alkoxy,cycloalkyloxy, aryloxy, heteroaryloxy, alkylsulfonyl, benzyl,alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl,heteroarylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, orheteroaryloxycarbonyl, where any of these groups may be unsubstituted orsubstituted with any of the functional groups represented by one or moreof the following: halogen, cyano, nitro, amino, carboxyl, alkyl,haloalkyl, alkylsilyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy,alkoxycarbonyl, haloalkoxy, haloalkoxycarbonyl, alkylsulfonyl,haloalkylsulfonyl, aryl, heteroaryl, or cycloalkyl; Q is a heterocycle,examples of which are as follows:

wherein R₁ is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, amino,alkoxyalkyl, acetyl, alkoxycarbonylamino, alkylcarbonylamino, oralkoxycarbonyl; R₂ is alkyl or haloalkyl; R₁ and R₂ could combine toform a five- or six-membered heterocyclic ring; R₃ is hydrogen, halogen,nitro, amino, alkylamino, haloalkylamino, cyano, or amide; R₈ and R₉ areindependently oxygen, sulfur, or imino group; Q6, Q7, and Q10 mayoptionally be unsaturated containing one or two double bonds in the6-membered ring; M is nitro.
 15. A compound represented by the followingformulae IV or V:

wherein X′ and Y′ are halogens; and R is hydrogen, alkyl, alkenyl,alkynyl, cycloalkyl, aryl, heteroaryl, alkoxy, cycloalkyloxy, aryloxy,heteroaryloxy, alkylsulfonyl, benzyl, alkylcarbonyl, alkenylcarbonyl,alkynylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl,aryloxycarbonyl, or heteroaryloxycarbonyl, where any of these groups maybe unsubstituted or substituted with any of the functional groupsrepresented by one or more of the following: halogen, cyano, nitro,amino, carboxyl, alkyl, haloalkyl, alkylsilyl, alkylcarbonyl,haloalkylcarbonyl, alkoxy, alkoxycarbonyl, haloalkoxy,haloalkoxycarbonyl, alkylsulfonyl, haloalkylsulfonyl, aryl, heteroaryl,or cycloalkyl.